WO2014104666A1 - Composition d'encre pour un élément électronique organique, et élément électronique organique l'utilisant - Google Patents

Composition d'encre pour un élément électronique organique, et élément électronique organique l'utilisant Download PDF

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WO2014104666A1
WO2014104666A1 PCT/KR2013/011964 KR2013011964W WO2014104666A1 WO 2014104666 A1 WO2014104666 A1 WO 2014104666A1 KR 2013011964 W KR2013011964 W KR 2013011964W WO 2014104666 A1 WO2014104666 A1 WO 2014104666A1
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ink composition
hrms
elemental analysis
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PCT/KR2013/011964
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Korean (ko)
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남동헌
이재훈
백영미
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주식회사 두산
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/32—Inkjet printing inks characterised by colouring agents
    • 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
    • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F7/00—Compounds containing elements of Groups 4 or 14 of the Periodic Table
    • C07F7/02—Silicon compounds
    • C07F7/08—Compounds having one or more C—Si linkages
    • C07F7/0803—Compounds with Si-C or Si-Si linkages
    • C07F7/0805—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms
    • C07F7/0807—Compounds with Si-C or Si-Si linkages comprising only Si, C or H atoms comprising Si as a ring atom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09D—COATING COMPOSITIONS, e.g. PAINTS, VARNISHES OR LACQUERS; FILLING PASTES; CHEMICAL PAINT OR INK REMOVERS; INKS; CORRECTING FLUIDS; WOODSTAINS; PASTES OR SOLIDS FOR COLOURING OR PRINTING; USE OF MATERIALS THEREFOR
    • C09D11/00—Inks
    • C09D11/30—Inkjet printing inks
    • C09D11/36—Inkjet printing inks based on non-aqueous solvents
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/13—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing
    • H10K71/135—Deposition of organic active material using liquid deposition, e.g. spin coating using printing techniques, e.g. ink-jet printing or screen printing using ink-jet printing
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K71/00—Manufacture or treatment specially adapted for the organic devices covered by this subclass
    • H10K71/10—Deposition of organic active material
    • H10K71/12—Deposition of organic active material using liquid deposition, e.g. spin coating
    • H10K71/15—Deposition of organic active material using liquid deposition, e.g. spin coating characterised by the solvent used
    • 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
    • H10K85/40—Organosilicon compounds, e.g. TIPS pentacene
    • 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
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • 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
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene

Definitions

  • the present invention relates to an ink composition for an organic electronic device including an anthracene-based compound, and an organic electronic device having improved characteristics such as efficiency, driving voltage, and lifetime using the ink composition.
  • An organic electronic device is an electronic device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and an organic semiconductor material.
  • Organic electronic devices may be classified into two types according to operating principles. First, when photons flow from an external light source into an organic material layer in an organic device, an exciton is formed in the organic material layer, and the exciton is separated into electrons and holes, and then transferred to another electrode to be used as a current source (voltage source). Is an electronic device. Second, when voltage or current is applied to two or more electrodes, holes and / or electrons are injected into the organic semiconductor material layer in contact with the electrode, and there is an organic electronic device in a form of operating by the injected electrons and holes.
  • Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC) drum, and an organic transistor. These all require electron / hole injection materials, electron / hole extraction materials, electron / hole transport materials or light emitting materials for driving the devices, and these materials operate on similar principles within each organic electronic device.
  • OPC organic photoconductor
  • the organic light emitting device generally has a structure including an anode, a cathode, and an organic material layer in the form of a thin film having semiconductor properties interposed therebetween.
  • a voltage is applied between two electrodes in the structure of the organic light emitting diode, holes are injected into the organic material layer at the anode and electrons are respectively formed at the anode, and excitons are generated when the injected holes and the electrons meet each other.
  • the excitons transition from the excited state (LUMO) to the ground state (HOMO), light in the visible region is emitted.
  • the display field is becoming larger.
  • the substrate has a large size, the production yield is lowered, the investment cost is increased, and the material is consumed, such as a fatal disadvantage.
  • HOMO and LUMO properties or energy (electron or hole) transition properties which dominate the luminescence properties, as well as glass, are prevented from decomposition at high evaporation temperatures. It has a high transition temperature (Tg) and its use is limited.
  • the present invention is to provide an ink composition excellent in printability and an organic electronic device using the same while improving the luminous efficiency, brightness, power efficiency, thermal stability and lifespan of the device.
  • the present invention (a) a compound represented by the following formula (1), (b) an aliphatic cyclic compound having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; Aromatic cyclic compounds having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; A first organic solvent selected from the group consisting of 5 to 20 heterocyclic compounds substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen, or containing a hetero atom selected from oxygen, sulfur and nitrogen, (c ) Different from the first organic solvent, alcohol solvent, ketone solvent, cellosolve solvent, carboxylic acid solvent, carbitol solvent, acetate solvent, lactate solvent, amine solvent, ether solvent, aromatic hydrocarbon
  • an ink composition for an organic electronic device comprising a second organic solvent selected from the group consisting of a solvent based on a solvent, an aliphatic hydrocarbon solvent, and an amide solvent:
  • R 1 to R 7 are the same or different, each independently represent hydrogen, deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 of the an aryl group, nuclear atoms of 5 to 40 heteroaryl group, C 6 ⁇ C 40 of the aryloxy group, C 1 ⁇ C 40 alkyloxy group of, C of 6 ⁇ C 40 arylamino group, C 6 ⁇ C 40 of Dia A arylamino group, a C 6 to C 40 arylalkyl group, a C 3 to C 40 cycloalkyl group, and a nuclear atom having 3 to 40 heterocycloalkyl groups, or a condensed aliphatic ring or condensed aromatic group in combination with an adjacent group A ring, a condensed heteroaliphatic ring, or a condensed heteroaromatic ring can be formed;
  • An arylalkyl group, a C 3 to C 40 cycloalkyl group and a nuclear atom having 3 to 40 heterocycloalkyl groups are each independently deuterium, halogen, nitrile group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 1 ⁇ C 40 of an amino group, an aryl group and the nucleus of a C 3 ⁇ C 40 heterocycloal
  • R 1 to R 4 are each independently a C 6 to C 40 aryl group.
  • the present invention is an organic electronic device comprising a first electrode, a second electrode, and at least one organic material layer interposed between the first electrode and the second electrode, at least one of the at least one organic material layer.
  • the present invention provides an organic electronic device comprising an organic thin film formed by using the ink composition according to any one of claims 1 to 3.
  • the organic thin film formed using the ink composition is preferably included in the light emitting layer.
  • the ink composition for an organic electronic device according to the present invention not only has excellent light emitting ability, but also has excellent printability.
  • the ink composition according to the present invention when used as an organic layer material of the organic electronic device, preferably a light emitting layer material, a large organic material having a multilayer structure having improved luminous efficiency, luminance, power efficiency, thermal stability, and lifetime compared to conventional light emitting materials Electronic devices can be easily manufactured, and further, full color display panels with greatly improved performance and lifetime can be manufactured.
  • the present invention provides an ink composition for an organic electronic device, comprising: (a) a compound represented by Chemical Formula 1, (b) an aliphatic cyclic compound having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur, and nitrogen; Aromatic cyclic compounds having 5 to 20 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; A first organic solvent selected from the group consisting of 5 to 20 heterocyclic compounds substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen, or containing a hetero atom selected from oxygen, sulfur and nitrogen, (c ) Different from the first organic solvent, alcohol solvent, ketone solvent, cellosolve solvent, carboxylic acid solvent, carbitol solvent, acetate solvent, lactate solvent, amine solvent, ether solvent, aromatic hydrocarbon And a second organic solvent selected from the group consisting of an aliphatic solvent, an aliphatic hydrocarbon solvent, and an amide solvent.
  • Such an ink composition not only has excellent
  • the ink composition according to the present invention includes a compound represented by Chemical Formula 1.
  • the compound is a monomolecular fluorescent material that is dissolved in the first solvent, and has a energy gap between the conduction band and the valence band in a range of about 0.1 to 5 eV.
  • the compound represented by the formula (1) is an anthracene derivative, a core in which an anthracene moiety having excellent device properties and a moiety such as fluorene having excellent fluorescence property are bonded to each other, for example, an indenoanthracene core. It is a compound which has an aryl group substituted by the said core.
  • R 1 to R 7 are the same as or different from each other, and each independently hydrogen, deuterium, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 Alkynyl group, C 6 ⁇ C 40 aryl group, heteroaryl group of 5 to 40 nuclear atoms, C 6 ⁇ C 40 aryloxy group, C 1 ⁇ C 40 alkyloxy group, C 6 ⁇ C 40 Arylamino group, C 6 ⁇ C 40 diarylamino group, (C 6 ⁇ C 40 aryl) C 1 ⁇ C 40 alkyl group, C 3 ⁇ C 40 cycloalkyl group and 3 to 40 heterocycloalkyl group Selected from the group consisting of; Or may be combined with adjacent groups to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.
  • An arylalkyl group, a C 3 to C 40 cycloalkyl group and a nuclear atom having 3 to 40 heterocycloalkyl groups are each independently deuterium, halogen, nitrile group, nitro group, C 1 to C 40 alkyl group, C 2 to C 40 Alkenyl group, C 1 to C 40 alkoxy group, C 1 to C 40 amino group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 40 ary
  • R 1 to R 7 wherein the C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 2 ⁇ C 40 alkynyl group, C 6 ⁇ C 40 of the aryl group, the number of nuclear atoms of 5 to the 40 heteroaryl groups, C 6 to C 40 aryloxy groups, C 1 to C 40 alkyloxy groups, C 6 to C 40 arylamino groups, C 6 to C 40 diarylamino groups, C 6 to C 40 C 1 -C 40 alkyl group, C 2 -C 40 alkenyl group, C 1- in the substituent introduced into a substituted arylalkyl group, C 3 ⁇ C 40 cycloalkyl group and a nuclear atom of 3 to 40 heterocycloalkyl group C 40 alkoxy group, C 1 -C 40 amino group, C 3 -C 40 cycloalkyl group, nuclear 3 to 40 heterocycloalkyl group, C 6 to C 40 aryl group and nuclear 5
  • R 1 to R 4 are each independently a C 6 ⁇ C 40 aryl group, preferably two or more of R 1 to R 4 are each independently C 6 ⁇ C 40 It is an aryl group selected from the group consisting of the structural formula of Formula 2 below.
  • R 1 to R 4 of R 1 and R 2; Or R 3 and R 4 ; Or R 1 , R 2 and R 3 ; Or R 1 , R 2 and R 4 ; Or R 1 , R 2 , R 3 and R 4 are each independently a C 6 ⁇ C 40 aryl group selected from the group consisting of the formula (2).
  • the Q 1 to Q 4 is a group the same or different and each independently represent hydrogen, deuterium, halogen, nitrile each other, a nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 of the Alkoxy group, C 1 to C 40 amino group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group, C 6 to C 40 aryl group and nuclear atom 5 to 40 heteroaryl group It may be selected from the group consisting of, or combine with adjacent groups to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring.
  • the cycloalkyl group, the heterocycloalkyl group of 3 to 40 nuclear atoms, the aryl group of C 6 ⁇ C 40 and the heteroaryl group of 5 to 40 nuclear atoms are each independently deuterium, halogen, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 to C 40 alkenyl group, C 1 to C 40 alkoxy group, C 1 to C 40 amino group, C 3 to C 40 cycloalkyl group, nuclear atom 3 to 40 heterocycloalkyl group , C 6 ⁇ C 40 It may be further unsubstituted or substituted with one or more third substituent selected from the group consisting of an aryl group and a heteroaryl group of 5 to 40
  • C 6 ⁇ C 40 aryl group selected from the group consisting of the structural formula of Formula 2 is phenyl, biphenyl, terphenyl, terphenyl, naphthyl, anthracenyl, Phenanthryl, pyrenyl, fluorenyl, fluoranthenyl, perylenyl, and the like.
  • aryl groups are each independently deuterium, halogen, nitrile group, nitro group, C 1 ⁇ C 40 alkyl group, C 2 ⁇ C 40 alkenyl group, C 1 ⁇ C 40 alkoxy group, C 1 ⁇ C 40 amino group, Or substituted with one or more selected from the group consisting of a C 3 to C 40 cycloalkyl group, a heterocycloalkyl group of 3 to 40 nuclear atoms, an aryl group of C 6 to C 40 , and a heteroaryl group of 5 to 40 nuclear atoms, Or may be combined with adjacent groups to form a condensed aliphatic ring, a condensed aromatic ring, a condensed heteroaliphatic ring or a condensed heteroaromatic ring or to form a spiro bond.
  • the content of the compound represented by Chemical Formula 1 is not particularly limited, and is preferably adjusted according to the type of solution coating method or the molecular weight of the compound.
  • the content of the compound represented by Formula 1 may be about 0.01 to 10% by weight, preferably about 0.1 to 5% by weight, more preferably about 0.1 to about 10% by weight based on the total weight of the ink composition. 3 weight percent.
  • the compound of Formula 1 may be synthesized according to a general synthesis method ( Chem. Rev. , 60 : 313 (1960); J. Chem. SOC . 4482 (1955); Chem. Rev. 95: 2457 (1995), etc. Reference). Detailed synthesis procedures for the compounds of the present invention will be described in detail in the preparation examples described below.
  • the ink composition according to the present invention comprises a first organic solvent.
  • the first organic solvent may adjust the viscosity of the ink composition while dissolving the compound of Formula 1.
  • the first organic solvent contains oxygen, sulfur or nitrogen in the ring, or an atom-containing functional group selected from oxygen, sulfur and nitrogen, an aromatic ring compound such as benzene or an aromatic group substituted with an alkyl group such as toluene Unlike the cyclic compound, the compound of Chemical Formula 1 may be well dissolved.
  • the first organic solvent is higher than the boiling point of the following second organic solvent, the first organic solvent is mixed with the following second organic solvent, thereby changing the viscosity of the ink composition or the ejection opening when forming the organic layer by inkjet printing or the like. Not only can the clogging be prevented, the stability of the ink composition can be improved, but also agglomeration of the applied ink composition can be prevented.
  • an aliphatic cyclic compound having 5 to 12 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen Aromatic cyclic compounds having 6 to 12 carbon atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen; And a heterocyclic compound having 5 to 12 nuclear atoms substituted with an atom-containing functional group selected from oxygen, sulfur and nitrogen, or containing a hetero atom selected from oxygen, sulfur and nitrogen, which are alone or two or more Can be used in combination.
  • the first organic solvent examples include methylcyclopentanol, furan, tetrahydrofuran, tetrahydrofurfuryl alcohol, pyrrole, pyrrolidine , 2-Pyrrolidone, Thiopene, Tetrahydrothiopene, Tetrahydrothiopene, Sulfurane, Pyran, Tetrahydropyran, Piperidine, Pyridine, trimethylpyridine, tripropylpyridine, morpholine, anisole, and the like, but are not limited thereto.
  • the boiling point of the first organic solvent is not particularly limited, but a low temperature process is possible when the boiling point is in the range of about 150 to 350 ° C, preferably about 200 to 350 ° C, more preferably 200 to 300 ° C.
  • the content of the first organic solvent is not particularly limited, but since the first organic solvent controls the viscosity of the ink composition while dissolving the compound of Formula 1, the content thereof is the content of the compound represented by Formula 1,
  • the content may be adjusted for the purpose of controlling the viscosity of the desired ink composition.
  • the content of the first organic solvent may be adjusted in the range of about 50 to 99.9 wt% based on the total weight of the ink composition.
  • the ink composition according to the present invention comprises a second organic solvent.
  • the second organic solvent may control not only the viscosity of the ink composition but also various properties such as hydrophilicity and hydrophobicity.
  • the second organic solvent used in the present invention alcohol solvent, ketone solvent, cellosolve solvent, carboxylic acid solvent, carbitol solvent, acetate solvent, lactate solvent, amine solvent, ether solvent, aromatic
  • hydrocarbon solvents, aliphatic hydrocarbon solvents, and amide solvents which may be used alone or in combination of two or more thereof.
  • the linearity of the ink composition during application Deterioration, clogging of the discharge port of the inkjet print, and the like can be prevented, and agglomeration of organic layers during drying and firing can be prevented.
  • Non-limiting examples of the alcohol solvent solvent include methanol, ethanol, propanol, isopropanol, butanol, isobutanol, pentanol, isopentanol, hexanol, heptanol, octanol, 1,3-propane diol, 1, 3-hexanediol, 1,4-octane diol and the like;
  • Non-limiting examples of the ketone solvent solvent include acetone, methyl ethyl ketone, methyl butyl ketone, methyl propyl ketone, cyclohexanone, benzophenone, acetophenone, hexyl methyl ketone and the like;
  • Non-limiting examples of the cellosolve solvent solvent is methyl cellosolve, ethyl cellosolve, propyl cellosolve, butyl cellosolve, and the like, non-limiting examples of carbitol solvent
  • Non-limiting examples of the acetate solvent solvent include ethyl acetate, propyl acetate, butyl acetate, amyl acetate, hexyl acetate, ethyl carbitol acetate and the like;
  • Non-limiting examples of the lactate solvent solvents include lactic acid, n-propyl lactate, isopropyl lactate, n-butyl lactate, isobutyl lactate, 2-ethylhexyl lactate and the like.
  • examples of the amine solvent solvent include propyl amine, isopropyl amine, butyl amine, isobutyl amine, amyl amine, hexyl amine, heptyl amine, octyl amine, 2-ethylhexyl amine, nonyl amine, decyl amine, lauryl Amine stearyl amine, oleyl amine, dibutyl amine, diamyl amine, dihexyl amine, diheptyl amine, dioctyl amine, dinonyl amine, didecyl amine, dilauryl amine, dioleyl amine, tripropyl amine, tri Butyl amine, triamyl amine, trihexyl amine, triheptyl amine, trioctylamine, trinonyl amine, tridecyl amine, trilauryl amine, cyclohex
  • non-limiting examples of the ether solvent include tetrahydrofuran, anisole, and the like
  • non-limiting examples of the aromatic hydrocarbon solvent include toluene, xylene, ethylbenzene, benzene, nitrobenzene, and the like.
  • Non-limiting examples of aliphatic hydrocarbon solvents include cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, chloroform, and the like.
  • Non-limiting examples of amide solvents include N-methyl-2-pi. Rollidone, N, N-dimethylacetamide, N, N-dimethylformamide and the like.
  • the boiling point of the second organic solvent is not particularly limited, but may be in the range of about 50 to 300 ° C., preferably about 150 to 300 ° C., more preferably about 200 to 250 ° C. At this time, two or more kinds having different boiling points may be mixed and used as the second organic solvent.
  • the content of the second organic solvent is not particularly limited, and it is appropriate to add the compound of Formula 1 dissolved in the ink composition in such a way that it does not elute, but is preferably about 0.1 to 50% by weight based on the total weight of the ink composition. When about 0.1 to 30% by weight, the viscosity and surface tension of the ink composition that is difficult to secure with only the first organic solvent can be secured at the same time.
  • the ink composition according to the present invention may further include an aromatic ketone solvent.
  • the aromatic ketone solvent used is different from the second organic solvent.
  • the aromatic ketone solvent may improve the dissolution stability of the ink composition.
  • aromatic ketone solvent examples include a tetraallon compound, and specifically, a C 1 to C 12 aliphatic hydrocarbon group, a C 6 to C 12 aryl group, and a heteroaryl group having 5 to 12 nuclear atoms.
  • aromatic ketone solvent other than the tetralral compound examples include acetophenone (methyl phenyl ketone), propiophenone (ethylphenyl ketone), benzophenone (diphenyl ketone), and derivatives thereof, but are not limited thereto.
  • the ink composition according to the present invention may further comprise a dopant material.
  • a dopant material By including the dopant material, not only does not only increase the luminous efficiency through the increase in color purity and energy transfer, but also the need for applying a dopant material when forming the light emitting layer of the device can be shortened the process.
  • the dopant material when the dopant material is not included in the ink composition, the light emitting layer may be formed through a vacuum deposition method, a solution coating method, or the like during the manufacture of the organic electronic device.
  • Examples of the dopant include alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, rare earth metal compounds, and halogen compounds and oxides thereof. These may be used alone or in combination of two or more thereof.
  • alkali metal examples include Li (work function: 2.93 eV), Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV)
  • alkali metals having a work function of 3.0 eV or less are preferred, for example, Li, K, Rb and Cs.
  • alkaline earth metal examples include Ca (work function: 2.9 eV), Sr (work function: 2.0 to 2.5 eV), Ba (work function: 2.52 eV), and an alkaline earth metal having a work function of 3.0 eV or less is preferable. .
  • rare earth metal examples include Sc, Y, Ce, Tb, and Yb, and a rare earth metal having a work function of 3.0 eV or less is preferable.
  • Preferred metals among these metals have particularly high reducing ability, so that by adding a relatively small amount of metal to the electron injection region, the light emission intensity of the organic EL device can be improved and the life can be extended.
  • alkali metal compound examples include alkali oxides such as Li 2 O, Cs 2 O or K 2 O; Alkali halides such as LiF, NaF, CsF or KF and the like, and alkali oxides or alkali fluorides such as LiF, Li 2 O or NaF are preferred.
  • alkaline earth metal compound examples include BaO, SrO, CaO, and mixtures thereof, such as Ba x Sr 1-x O (0 ⁇ x ⁇ 1) and Ba x Ca 1-x O (0 ⁇ x ⁇ 1) Etc. Among these, BaO, SrO and CaO are preferable.
  • rare earth metal compound examples include YbF 3 , ScF 3 , ScO 3 , Y 2 O 3 , Ce 2 O 3 , GdF 3 and TbF 3 , among which YbF 3 , ScF 3 and TbF 3 are preferable.
  • the alkali metal complex, alkaline earth metal complex and rare earth metal complex are not particularly limited as long as they each contain one or more alkali metal ions, alkaline earth metal ions and rare earth metal ions as metal ions.
  • preferred examples of the ligand include quinolinol, benzoquinolinol, akyridinol, phenantridinol, hydroxyphenyl oxazole, hydroxyphenyl thiazole, hydroxy diaryl oxadiazole, and hydroxy diaryl thiazole.
  • Hydroxyphenylpyridine Hydroxyphenylpyridine, hydroxyphenylbenzoimidazole, hydroxybenzotriazole, hydroxyflubolane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines , And derivatives thereof, but are not limited thereto.
  • the content of the dopant material is not particularly limited, but may be about 1 to 99% by weight, preferably about 1 to 30% by weight, and more preferably about 5 to 20% by weight, based on the total weight of the dry solid film.
  • a dry thin film means the thin film formed by apply
  • the ink composition according to the present invention is an antifoaming agent that removes air bubbles in the ink composition other than the compound of Formula 1, the first organic solvent, and the second organic solvent within a range that does not significantly impair the object and effect of the present invention ( Degassing agent, Leveling agent that contributes to planarization during formation of organic layer, Slip agent to improve printability in substrate surface contact printing process, Wetting agent to increase adhesion of organic layer to substrate surface agent), and may further include one or more additives such as thickeners and surfactants to increase the viscosity of the ink composition and improve the formability of the organic layer.
  • Degassing agent Leveling agent that contributes to planarization during formation of organic layer
  • Slip agent to improve printability in substrate surface contact printing process
  • Wetting agent to increase adhesion of organic layer to substrate surface agent
  • additives such as thickeners and surfactants to increase the viscosity of the ink composition and improve the formability of the organic layer.
  • the polymer may further include polymer materials such as acrylic resins, modified acrylic resins, epoxy resins, modified epoxy resins, urethane resins, modified urethane resins, silicone resins, modified silicone resins, fluorocarbon resins, and modified fluorocarbon resins. Can be.
  • polymer materials such as acrylic resins, modified acrylic resins, epoxy resins, modified epoxy resins, urethane resins, modified urethane resins, silicone resins, modified silicone resins, fluorocarbon resins, and modified fluorocarbon resins. Can be.
  • the content of the additive is not particularly limited, it is appropriate to use within the range that the properties of the dried organic layer is not degraded, for example, about 0.001 to 1% by weight, preferably about about the total weight of the ink composition It may be 0.001 to 0.1% by weight.
  • the ink composition of the present invention can be prepared through various methods.
  • the ink composition may be prepared by dissolving the compound represented by Chemical Formula 1 in the first organic solvent and then adding the second organic solvent.
  • the second organic solvent when the second organic solvent is added, an aromatic ketone solvent and / or a dopant material may be further added, and one or more additives described above may be further added.
  • the viscosity of the ink composition described above is preferably adjusted by appropriately selecting the type and content of the compound represented by the formula (1), the first and second organic solvents according to the solution coating method. For example, it may be about 1 to 100 cps, preferably about 3 to 50 cps. According to an example of the present invention, when forming the organic layer through inkjet printing, the viscosity of the ink composition may be adjusted to about 3 to 25 cps, preferably about 3 to 20 cps.
  • the surface tension of the ink composition varies depending on the type of the compound represented by Formula 1, the first and second organic solvents, about 1 to 100 dyne / cm 2 , preferably about 10 to 60 dyne / cm 2 , and more. Preferably about 15-40 dyne / cm 2 .
  • the present invention provides an organic electronic device, preferably an organic electroluminescent device using the ink composition described above.
  • the organic electronic device includes a first electrode, a second electrode, one or more organic material layers interposed between the first electrode and the second electrode, and at least one of the one or more organic material layers is the ink. It includes an organic thin film formed using the composition.
  • the method of manufacturing the organic electronic device of the present invention is that the ink composition is applied onto a substrate through a known solution coating method, and then the coating layer is cured by light irradiation or heat treatment to form one or more organic material layers.
  • examples of the solution coating method are spin coating method, dip coating method, inkjet printing method, screen printing method, gravure printing method, flexographic printing method, slot die coating method, coating method using a doctor blade and various roll coating methods And the like, but are not limited thereto.
  • Examples of such an organic electronic device include an organic electroluminescent device, an organic field effect transistor (OFET), an organic thin film transistor (OTFT), an organic photoconductor (OPC) drum, an organic photovoltaic device, and an organic solar cell.
  • OFET organic field effect transistor
  • OFT organic thin film transistor
  • OPC organic photoconductor
  • the organic electroluminescent device includes an anode, a cathode, and one or more organic material layers interposed between the anode and the cathode.
  • the at least one organic material layer may be any one or more of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer, at least one of the organic material layer comprises an organic thin film formed using the ink composition, preferably
  • the light emitting layer may include an organic thin film formed using the ink composition.
  • the structure of the organic electroluminescent device is not particularly limited, and may be, for example, a structure in which a substrate, an anode, a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and a cathode are sequentially stacked.
  • at least one of the hole injection layer, the hole transport layer, the light emitting layer, the electron transport layer and the electron injection layer may include an organic thin film formed of the ink composition, preferably the light emitting layer comprises an organic thin film formed of the ink composition.
  • an electron injection layer may be further stacked on the electron transport layer.
  • an insulating layer or an adhesive layer may be further inserted at an interface between the electrode and the organic material layer.
  • the organic electroluminescent device according to the present invention may be formed of another organic material layer using materials and methods known in the art, except that one or more layers (eg, a light emitting layer) of the organic material layer are formed by solution coating the ink composition. It can be manufactured by forming an electrode.
  • one or more layers eg, a light emitting layer of the organic material layer are formed by solution coating the ink composition. It can be manufactured by forming an electrode.
  • the other organic material layer not formed of the ink composition may be formed by a vacuum deposition method or a solution coating method.
  • the solution coating method include, but are not limited to, spin coating, dip coating, doctor blading, inkjet printing, or thermal transfer.
  • the substrate usable in the present invention is not particularly limited, and silicon wafers, quartz, glass plates, metal plates, plastic films, sheets, and the like may be used.
  • examples of the anode 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); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as polythiophene, poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDT), polypyrrole or polyaniline; And carbon black, but are not limited thereto.
  • 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); Combinations of metals and oxides such as ZnO: Al or SnO 2 : Sb
  • Conductive polymers such as polythiophene, poly (3-methylthiophene
  • the negative electrode material may be a metal such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, or lead or an alloy thereof; And multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like.
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, it is preferable that the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material 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 electron transporting material a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer 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 organic electroluminescent 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 ink composition according to the present invention may act on a similar principle to that applied to organic electroluminescent devices in other organic electronic devices such as organic solar cells, organic photoconductors, and organic transistors.
  • intermediate EMI 2 could be obtained using 2-bromo-9,9-dimethyl-9H-fluorene instead of 2-Bromonaphthrene.
  • EMI3 was obtained by using 4-bromobiphenyl instead of 2-Bromonaphthrene in ⁇ Step 3> of Synthesis Example 1-1.
  • intermediate EMI 4 could be obtained using 3-bromofluoranthene instead of 2-Bromonaphthrene.
  • EMI 6 was obtained by using 2-bromo-9,9-dimethyl-9H-fluorene instead of 2-Bromonaphthrene used in ⁇ Step 3> of Synthesis Example 2-1.
  • EMI 7 was obtained by using 4-bromobiphenyl instead of 2-Bromonaphthrene used in ⁇ Step 3> of Synthesis Example 2-1.
  • EMI8 was obtained by using 3-bromofluoranthene instead of 2-Bromonaphthrene used in ⁇ Step 3> of Synthesis Example 2-1.
  • Example 1-1 except for using the compounds Inv 1-2 to Inv 1-20 synthesized in Synthesis Examples 1-6 to 1-24, respectively, instead of the compound Inv 1-1 used in Example 1-1. In the same manner as in the ink compositions 1-2 to 1-20 were prepared.
  • Examples 1-21 except for using the compounds Inv 1-22 to Inv 1-40 synthesized in Synthesis Examples 1-26 to 1-44 instead of the compound Inv 1-21 used in Example 1-21 In the same manner as in the ink compositions 1-22 to 1-40 were prepared.
  • Example 2-1 except for using the compounds Inv 2-2 to Inv 2-12 synthesized in Synthesis Examples 2-6 to 2-16 instead of the compound Inv 2-1 used in Example 2-1 In the same manner as in the ink compositions 2-1 to 2-12 were prepared.
  • Example 2-13 except for using the compounds Inv 2-14 to Inv 2-24 synthesized in Synthesis Examples 2-18 to 2-28, respectively, instead of the compound Inv 2-13 used in Example 2-13. In the same manner as in the ink compositions 2-14 to 2-24 were prepared.
  • Example 2-25 except for using the compounds Inv 2-26 to Inv 2-36 synthesized in Synthesis Examples 2-30 to 2-40 instead of the compound Inv 2-25 used in Examples 2-25 In the same manner as in the ink compositions 2-26 to 2-36 were prepared.
  • Example 2-37 except for using the compounds Inv 2-38 to Inv 2-48 synthesized in Synthesis Examples 2-42 to 2-52, respectively, instead of the compound Inv 2-37 used in Example 2-37 In the same manner as in the ink compositions 2-38 to 2-48 were prepared.
  • Example 3-1 except for using the compounds Inv 3-2 to Inv 3-29 synthesized in Synthesis Examples 3-4 to 3-31, respectively, instead of the compound Inv 3-1 used in Example 3-1 In the same manner as in the ink compositions 3-2 to 3-29 were prepared.
  • Example 4-1 except for using the compounds Inv 4-2 to Inv 4-30 synthesized in Synthesis Examples 4-5 to 4-33, respectively, instead of the compound Inv 4-1 used in Example 4-1. In the same manner as in the ink compositions 4-2 to 4-30 were prepared.
  • Example 5-1 except for using the compounds Inv 5-2 to Inv 5-47 synthesized in Synthesis Examples 5-3 to 5-48, respectively, instead of the compound Inv 5-1 used in Example 5-1 In the same manner as in the ink compositions 5-2 to 5-47 were prepared.
  • an organic electroluminescent device was manufactured by the following method.
  • the glass substrate coated with ITO Indium tin oxide
  • ITO Indium tin oxide
  • a solvent such as isopropyl alcohol, acetone, methanol and the like
  • the substrate is cleaned for 5 minutes using an oxygen plasma, and then the substrate is transferred to a vacuum depositor. It was.
  • a hole injection layer was formed by thermal vacuum deposition of DS-HIL (Doosan Co., Ltd.) at a thickness of 800 kPa on the prepared ITO (anode), and a-NPB (N, N-di, which is a hole transport material, was formed on the hole injection layer.
  • DS-HIL Doosan Co., Ltd.
  • N-di N-di, which is a hole transport material
  • the ink composition 1-1 prepared in Example 1-1 was printed and fired on the hole transport layer using a spin coater or an inkjet printer under the conditions of the printing process glovebox to host-Dopant-based A light emitting layer was formed.
  • an electron transporting layer was formed by vacuum depositing Alq 3 , which is an electron transporting material, to a thickness of 250 kPa on the light emitting layer, and then an electron injection layer was formed by depositing LiF, which is an electron injecting material, to a thickness of 10 kW.
  • LiF which is an electron injecting material
  • Preparation Example 1 Alq 3 was used as the host material on the hole transport layer instead of forming the light emitting layer using the ink composition 1-1 on the hole transport layer, and C-545T (10- (2- benzothiazolyl) -1,1,7,7-tetramethyl-2,3,6,7-tetrahydro-1H, 5H, 11H- [1] benzopyrano [6,7,8-ij] -quinolizin-11-one) 5
  • An organic electroluminescent device was manufactured in the same manner as in Preparation Example 1, except that the light emitting layer was doped with% to form a light emitting layer by vacuum deposition at a thickness of 300 kPa. The structure of the organic EL device thus manufactured is shown in Table 1 below.
  • HIL Hole injection layer
  • HTL Hole Transport Layer
  • EML Organic light emitting layer
  • ETL Electron Transport Layer
  • EIL Electron injection layer

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Abstract

La présente invention concerne une composition d'encre, qui comprend un composé à base d'anthracène, pour un élément électronique organique et un élément électronique organique ayant des propriétés améliorées, telles qu'une efficacité, une tension d'attaque et une durée de vie, par utilisation de ladite composition d'encre.
PCT/KR2013/011964 2012-12-28 2013-12-20 Composition d'encre pour un élément électronique organique, et élément électronique organique l'utilisant WO2014104666A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN105367372A (zh) * 2015-11-16 2016-03-02 黑龙江省科学院石油化学研究院 用于有机电致发光显示的取代茚并[1,2-b]蒽类化合物及其制备方法
CN107001324A (zh) * 2014-10-29 2017-08-01 喜星素材株式会社 含氮多环化合物及使用其的有机发光器件

Families Citing this family (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102293729B1 (ko) * 2014-08-14 2021-08-27 삼성디스플레이 주식회사 축합환 화합물 및 이를 포함한 유기 발광 소자
JP6550830B2 (ja) 2015-03-25 2019-07-31 セイコーエプソン株式会社 機能層形成用組成物、機能層形成用組成物の製造方法、有機ｅｌ素子の製造方法、有機ｅｌ装置、電子機器

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080101793A (ko) * 2007-05-17 2008-11-21 주식회사 엘지화학 신규한 안트라센 유도체 및 이를 이용한 유기전자소자
KR20090118859A (ko) * 2008-05-14 2009-11-18 주식회사 두산 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
KR20110102904A (ko) * 2008-12-18 2011-09-19 메르크 파텐트 게엠베하 안트라〔２,３-ｂ〕벤조〔ｄ〕티오펜 유도체 및 유기 반도체로서의 이의 용도

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR20080101793A (ko) * 2007-05-17 2008-11-21 주식회사 엘지화학 신규한 안트라센 유도체 및 이를 이용한 유기전자소자
KR20090118859A (ko) * 2008-05-14 2009-11-18 주식회사 두산 안트라센 유도체 및 이를 이용한 유기 전계 발광 소자
KR20110102904A (ko) * 2008-12-18 2011-09-19 메르크 파텐트 게엠베하 안트라〔２,３-ｂ〕벤조〔ｄ〕티오펜 유도체 및 유기 반도체로서의 이의 용도

Cited By (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN107001324A (zh) * 2014-10-29 2017-08-01 喜星素材株式会社 含氮多环化合物及使用其的有机发光器件
CN107001324B (zh) * 2014-10-29 2020-09-22 Lt素材株式会社 含氮多环化合物及使用其的有机发光器件
CN105367372A (zh) * 2015-11-16 2016-03-02 黑龙江省科学院石油化学研究院 用于有机电致发光显示的取代茚并[1,2-b]蒽类化合物及其制备方法

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