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WO2019066337A1 - Composé, composition de revêtement le comprenant, diode électroluminescente organique l'utilisant, et son procédé de préparation - Google Patents

Composé, composition de revêtement le comprenant, diode électroluminescente organique l'utilisant, et son procédé de préparation Download PDF

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Publication number
WO2019066337A1
WO2019066337A1 PCT/KR2018/010841 KR2018010841W WO2019066337A1 WO 2019066337 A1 WO2019066337 A1 WO 2019066337A1 KR 2018010841 W KR2018010841 W KR 2018010841W WO 2019066337 A1 WO2019066337 A1 WO 2019066337A1
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substituted
unsubstituted
same
compound
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English (en)
Korean (ko)
Inventor
신현아
강성경
김광현
배재순
이재철
정재학
이충환
박형일
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LG Chem Ltd
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LG Chem Ltd
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Priority claimed from KR1020180109385A external-priority patent/KR102141281B1/ko
Application filed by LG Chem Ltd filed Critical LG Chem Ltd
Priority to CN201880019908.3A priority Critical patent/CN110520407B/zh
Priority to US16/491,386 priority patent/US11274213B2/en
Priority to JP2019547493A priority patent/JP6820057B2/ja
Publication of WO2019066337A1 publication Critical patent/WO2019066337A1/fr
Anticipated expiration legal-status Critical
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C217/00—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton
    • C07C217/78—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C217/94—Compounds containing amino and etherified hydroxy groups bound to the same carbon skeleton having amino groups and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings being part of condensed ring systems and etherified hydroxy groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • 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
    • C09D4/00—Coating compositions, e.g. paints, varnishes or lacquers, based on organic non-macromolecular compounds having at least one polymerisable carbon-to-carbon unsaturated bond ; Coating compositions, based on monomers of macromolecular compounds of groups C09D183/00 - C09D183/16
    • 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]
    • 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
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants
    • 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
    • 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

Definitions

  • the present invention relates to a compound, a coating composition comprising the compound, an organic light emitting device formed using the coating composition, and a method of manufacturing the same.
  • the organic light emission phenomenon is one example in which current is converted into visible light by an internal process of a specific organic molecule.
  • the principle of organic luminescence phenomenon is as follows. When an organic layer is positioned between the anode and the cathode, electrons and holes are injected into the organic layer from the cathode and the anode, respectively, when an electric current is applied between the two electrodes. Electrons and holes injected into the organic layer are recombined to form an exciton, and the exciton falls back to the ground state to emit light.
  • An organic light emitting device using such a principle may be generally composed of an organic material layer including a cathode, an anode and an organic material layer disposed therebetween, for example, a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer.
  • a deposition process has been mainly used for manufacturing an organic light emitting device.
  • a material loss is generated much when the organic light emitting device is manufactured by a deposition process.
  • a technique of manufacturing a device through a solution process which can increase production efficiency due to low material loss
  • development of a material that can be used in a solution process is required.
  • Materials used in organic light emitting devices for solution processes should have the following properties.
  • the material used in the solution process should have excellent coatability so that a thin film of uniform thickness can be formed without forming holes or aggregation when forming the thin film.
  • the layers to be subjected to the solution process must have resistance to the solvent and the material used in the process of forming the other layers, have excellent current efficiency in the production of the organic light emitting device, and have excellent lifetime characteristics.
  • L and L1 to L4 are the same or different and each independently represents a substituted or unsubstituted arylene group
  • Ar 1 and Ar 2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Y1 to Y4 are the same or different from each other, and each independently - (R101) s; Or -X-A, at least two of Y1 to Y4 are -X-A,
  • R101 is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aryloxy group,
  • s is an integer of 0 to 5, and when s is 2 or more, two or more R 101 s are the same or different from each other,
  • X is O or S
  • A is a functional group capable of crosslinking by heat or light
  • n1 and n4 are each an integer of 0 to 4,
  • n2 and n3 are each an integer of 0 to 3
  • n1 to n4 are each 2 or more, the substituents in the parentheses are the same or different from each other.
  • the present disclosure provides coating compositions comprising such compounds.
  • the disclosure also relates to a light emitting device comprising: a first electrode; A second electrode; And at least one organic layer disposed between the first electrode and the second electrode, wherein at least one of the organic layers includes a cured product of the coating composition.
  • the present disclosure provides a method of manufacturing a semiconductor device, comprising: preparing a substrate; Forming a first electrode on the substrate; Forming at least one organic layer on the first electrode; And forming a second electrode on the organic material layer, wherein the forming the organic material layer includes forming one or more organic material layers using the coating composition. do.
  • the compound according to one embodiment of the present invention can be subjected to a solution process and can be used as a material for an organic material layer of an organic light emitting device and can provide a low driving voltage, a high luminous efficiency and a high lifetime .
  • a compound according to one embodiment of the present disclosure forms a thin film that is completely cured from heat treatment or UV treatment below 220 ⁇ ⁇ , thereby forming a stable thin film that is not damaged from the next solution process.
  • FIG 1 shows an example of an organic light emitting device according to an embodiment of the present invention.
  • An embodiment of the present invention provides a compound represented by the following formula (1).
  • L and L1 to L4 are the same or different and each independently represents a substituted or unsubstituted arylene group
  • Ar 1 and Ar 2 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R1 to R4 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Y1 to Y4 are the same or different from each other, and each independently - (R101) s; Or -X-A, at least two of Y1 to Y4 are -X-A,
  • R101 is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted aryloxy group,
  • s is an integer of 0 to 5, and when s is 2 or more, two or more R 101 s are the same or different from each other,
  • X is O or S
  • A is a functional group capable of crosslinking by heat or light
  • n1 and n4 are each an integer of 0 to 4,
  • n2 and n3 are each an integer of 0 to 3
  • n1 to n4 are each 2 or more, the substituents in the parentheses are the same or different from each other.
  • the compound according to one embodiment of the present invention forms a stable thin film that is completely cured from heat treatment or UV treatment, as it contains oxygen (O) or sulfur (S) atoms in the compound.
  • the compound according to one embodiment of the present invention includes an alkyl group, an alkoxy group, and an aryloxy group in the compound, thereby having high affinity with a hydrocarbon series and / or ether series solvent, And has resistance to a solvent used in forming a layer other than the organic compound layer containing the compound by a solution process, thereby preventing migration to another layer.
  • a member when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.
  • the compound of formula (1) is preferably a compound having solubility in a suitable organic solvent.
  • the organic light emitting device can be manufactured by the solution coating method, and the device can be made larger.
  • &quot functional group capable of crosslinking by heat or light " may mean a reactive substituent which causes crosslinking between the compounds by exposure to heat and / or light.
  • the crosslinking can be produced by heat treatment or light irradiation, and connecting the radicals generated by decomposition of the carbon-carbon multiple bond, cyclic structure.
  • Quot refers to a moiety bonded to another substituent or bond.
  • " substituted " means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, When two or more substituents are substituted, two or more substituents may be the same as or different from each other.
  • the term " substituted or unsubstituted" A halogen group; A nitrile group; Silyl group; Boron group; An alkyl group; A cycloalkyl group; An alkoxy group; An aryloxy group; An aryl group; And a heterocyclic group, or a substituted or unsubstituted one in which at least two of the above-exemplified substituents are connected to each other.
  • " a substituent to which at least two substituents are connected &quot may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • the halogen group is fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • the silyl group may be represented by the formula of -SiR a R b R c , wherein R a , R b and R c are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the silyl group specifically includes, but not limited to, trimethylsilyl, triethylsilyl, tert-butyldimethylsilyl, vinyldimethylsilyl, propyldimethylsilyl, triphenylsilyl, diphenylsilyl and phenylsilyl. Do not.
  • the boron group may be represented by the formula of -BR d R e , wherein R d and R e are each hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group specifically includes, but is not limited to, a trimethylboron group, a triethylboron group, a tert-butyldimethylboron group, a triphenylboron group, and a phenylboron group.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but may be 1 to 60. According to one embodiment, the alkyl group may have 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include methyl, ethyl, propyl, isopropyl, n-butyl, isobutyl, tert-butyl, n-pentyl, n- .
  • the cycloalkyl group is not particularly limited, but may have 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 40 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. Specific examples of the cycloalkyl group include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, and may be 1 to 20 carbon atoms.
  • Specific examples of the alkoxy group include a methoxy group, an ethoxy group, an n-propoxy group, a n-butoxy group, a tert-butoxy group, a n-pentyloxy group, N-decyloxy group, n-decyloxy group, n-decyloxy group, and the like.
  • the aryl group is not particularly limited, but may have 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the aryl group has 6 to 30 carbon atoms. According to one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group examples include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a klycenyl group and a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heterocyclic group is a heterocyclic group and is a heterocyclic group containing at least one of N, O, P, S, Si and Se, and the number of carbon atoms is not particularly limited, but may be 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30. According to another embodiment, the number of carbon atoms of the heterocyclic group is 2 to 20.
  • the heterocyclic group include pyridyl, pyrrolyl, pyrimidyl, pyridazinyl, furanyl, thiophene, benzothiophene, benzofurane, dibenzothiophene, However, the present invention is not limited thereto.
  • heterocyclic group in the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.
  • the aryl group in the aryloxy group applies the description of the aryl group described above.
  • L is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
  • L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylene group.
  • L is a substituted or unsubstituted phenylene group; Or a substituted or unsubstituted biphenylylene group, the conjugated structure of the phenylene group or the biphenylylene group enables the hole to be moved smoothly so that it can have an energy level suitable for hole injection and hole transport,
  • the organic electroluminescent device has a low driving voltage, high luminous efficiency, and excellent lifetime characteristics.
  • L may be represented by the following formula (1-A) or (1-B).
  • R11 to R13 are the same or different from each other and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • n1 to m3 each represent an integer of 0 to 4,
  • R11 to R13 are the same 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 C1-C20 alkoxy group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • R11 to R13 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C30 heteroaryl group.
  • R11 to R13 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C30 heteroaryl group.
  • R11 to R13 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted n-butyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted dibenzofurane group.
  • R11 to R13 are the same or different and each independently hydrogen; heavy hydrogen; Methyl group; An ethyl group; n-propyl group; an n-butyl group; tert-butyl group; A phenyl group; A biphenyl group; Or a dibenzofurane group.
  • R11 to R13 are hydrogen.
  • m1 to m3 are each 0 or 1.
  • Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted C6 to C60 aryl; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • Ar 1 and Ar 2 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted C2-C30 heteroaryl group.
  • Ar 1 and Ar 2 are the same or different and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar 1 and Ar 2 are the same or different and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; Or a substituted or unsubstituted naphthyl group.
  • Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; A biphenyl group; A terphenyl group; Or a naphthyl group.
  • R 1 to R 4 are the same 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 C1-C20 alkoxy group; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • R 1 to R 4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C30 heteroaryl group.
  • R 1 to R 4 are the same or different and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted dibenzofurane group.
  • R 1 to R 4 are the same or different and each independently hydrogen; heavy hydrogen; Methyl group; An ethyl group; A phenyl group; A biphenyl group; A dibenzothiophene group; Or a dibenzofurane group.
  • R 2 and R 3 are hydrogen and R 1 and R 4 are phenyl groups.
  • R 1 to R 4 are hydrogen.
  • n1 to n4 are each 0 or 1.
  • Y1 to Y4 are the same or different from each other, and each independently - (R101) s; Or -X-A, and at least two of Y1 to Y4 are -X-A.
  • Y1 to Y4 are the same or different and are each independently - (R101) s; Or -X-A, and two of Y1 to Y4 are -X-A.
  • Y1 and Y4 are the same or different from each other, and each independently -X-A and Y2 and Y3 are - (R101) s.
  • Y1 and Y2 are the same or different, and are each independently -X-A, and Y3 and Y4 are - (R101) s.
  • Y1, Y2 and Y4 are the same or different from each other, and each independently -X-A and Y3 are - (R101) s.
  • Y1 to Y4 are the same or different and are each independently -X-A.
  • X is O or S.
  • A is a functional group capable of crosslinking by heat or light.
  • the functional group capable of crosslinking by heat or light may be any one of the following structures.
  • T1 is hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms,
  • T2 to T4 are the same or different and each independently represent a substituted or unsubstituted alkyl group having 1 to 6 carbon atoms.
  • T1 is hydrogen; Or a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted n-butyl group; Or a substituted or unsubstituted tert-butyl group.
  • T1 is hydrogen; Or a methyl group; An ethyl group; n-propyl group; an n-butyl group; Or a tert-butyl group.
  • T2 to T4 are the same or different and are each independently a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted n-propyl group; A substituted or unsubstituted n-butyl group; Or a substituted or unsubstituted tert-butyl group.
  • each of T2 to T4 is the same or different and is independently a methyl group; An ethyl group; n-propyl group; an n-butyl group; Or a tert-butyl group.
  • s is an integer of 0 to 2, and when s is 2, two R 101 s are the same or different from each other.
  • R101 is hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted aryloxy group having 4 to 30 carbon atoms.
  • R101 is hydrogen; heavy hydrogen; A halogen group; An alkyl group having 1 to 20 carbon atoms; An alkoxy group having 1 to 20 carbon atoms which is substituted or unsubstituted with an alkoxy group having 1 to 20 carbon atoms; An aryl group having 6 to 30 carbon atoms; Or an aryloxy group having 6 to 30 carbon atoms.
  • R101 is hydrogen; heavy hydrogen; Fluorine (-F); A substituted or unsubstituted methyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted ethoxy group; A substituted or unsubstituted ethylhexyloxy group; Or a substituted or unsubstituted phenyloxy group.
  • R101 is selected from the group consisting of hydrogen; heavy hydrogen; Fluorine (-F); Methyl group; Butyl group; Methoxy group; An ethoxy group substituted or unsubstituted with an alkoxy group having 1 to 20 carbon atoms; Ethylhexyloxy group; Or a phenyloxy group.
  • R101 is selected from the group consisting of hydrogen; heavy hydrogen; Fluorine (-F); Methyl group; tert-butyl group; Methoxy group; An ethoxy group substituted or unsubstituted with an ethoxy group; 2-ethylhexyloxy group; Or a phenyloxy group.
  • L1 to L4 are the same or different and each independently represent a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
  • L1 to L4 are the same or different and each independently represent a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 to L4 are the same or different from each other and each independently represents a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms And a substituted or unsubstituted arylene group having 6 to 30 carbon atoms which is substituted or unsubstituted with at least one substituent selected from the group consisting of an aryloxy group having 6 to 30 carbon atoms.
  • L1 to L4 are the same or different and each independently represent a substituted or unsubstituted C1 to C20 alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, An arylene group having 6 to 30 carbon atoms, which is substituted or unsubstituted with at least one substituent selected from the group consisting of an alkyl group, an alkoxy group and an aryloxy group having 6 to 30 carbon atoms.
  • L1 to L4 are the same or different and each independently represents a halogen group, a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms And a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; Or a substituted or unsubstituted alkyl group having 1 to 20 carbon atoms, a substituted or unsubstituted alkoxy group having 1 to 20 carbon atoms, and a substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms. Or an unsubstituted naphthylene group.
  • L1 to L4 are the same or different from each other, and each independently represents fluorine (-F), a substituted or unsubstituted methyl group, a substituted or unsubstituted tert-butyl group, a substituted or unsubstituted A substituted or unsubstituted methoxy group, a substituted or unsubstituted ethoxy group, a substituted or unsubstituted 2-ethylhexyloxy group and a substituted or unsubstituted phenyloxy group; A substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxy group, a substituted or unsubstituted alkoxy group, and a naphthylene group substituted or
  • L1 to L4 are the same or different and are each independently a phenylene group; Naphthylene group; Fluorophenylene groups; Methylphenylene group; A dimethylphenylene group; tert-butylphenylene group; A methoxyphenylene group; Ethoxyethoxyphenylene group; A phenyloxyphenylene group; Or a 2-ethylhexyloxyphenylene group.
  • the formula (1) may be represented by any one of the following formulas (2) to (5).
  • R1 to R4, n1 to n4, Ar1, Ar2 and L are the same as defined in formula (1)
  • X1 to X4 are the same or different and each independently O or S,
  • a 1 to A 4 are the same or different and are each independently a functional group capable of crosslinking by heat or light,
  • R21 to R26 are the same or different from each other, and each independently hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • p1 and p2 are each an integer of 0 to 5
  • p3 and p4 are each an integer of 0 to 4,
  • p5 and p6 are each an integer of 0 to 7,
  • R21 to R26 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group having 1 to 20 carbon atoms; A substituted or unsubstituted C1-C20 alkoxy group; A substituted or unsubstituted aryloxy group having 6 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted C2-C30 heteroaryl group.
  • R21 to R26 are the same or different and each independently hydrogen; Fluorine (-F); A substituted or unsubstituted methyl group; A substituted or unsubstituted tert-butyl group; A substituted or unsubstituted methoxy group; A substituted or unsubstituted ethoxy group; A substituted or unsubstituted hexyloxy group; Or a substituted or unsubstituted phenyloxy group.
  • R21 to R26 are independently selected from the group consisting of hydrogen; Fluorine (-F); Methyl group; tert-butyl group; Methoxy group; Ethoxyethoxy group; 2-ethylhexyloxy group; Or a phenyloxy group.
  • p1 to p6 are each 0 or 1.
  • the formula (1) may be represented by any one of the following compounds 1 to 140.
  • the compound according to one embodiment of the present specification can be produced by a production method described below.
  • the compound of Formula 1 can be prepared as a core structure as shown in Reaction Scheme 1 below.
  • Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.
  • a coating composition comprising a compound of formula 1 as described above.
  • the coating composition comprises the compound of Formula 1 and a solvent.
  • the coating composition may be in a liquid phase.
  • the "liquid phase” means that the liquid phase is at normal temperature and pressure.
  • the solvent includes, for example, chlorinated solvents such as chloroform, methylene chloride, 1,2-dichloroethane, 1,1,2-trichloroethane, chlorobenzene and o-dichlorobenzene; Ether solvents such as tetrahydrofuran and dioxane; Aromatic hydrocarbon solvents such as toluene, xylene, trimethylbenzene and mesitylene; Aliphatic hydrocarbon solvents such as cyclohexane, methylcyclohexane, n-pentane, n-hexane, n-heptane, n-octane, n-nonane and n-decane; Ketone solvents such as acetone, methyl ethyl ketone, cyclohexanone, isophorone, tetralone, decalone, and acetylacetone; Ester solvents such as e
  • the solvents may be used alone or in combination of two or more solvents.
  • the coating composition further comprises no p-doping material.
  • the coating composition further comprises a p-doping material.
  • the p-doped material means a material that has a p-type semiconductor property as a host material.
  • p semiconductor property means a property of injecting or transporting holes at a highest occupied molecular orbital (HOMO) energy level, that is, a material having a high conductivity of holes.
  • HOMO highest occupied molecular orbital
  • the p-doped material may be represented by any one of the following formulas (A) to (H), but is not limited thereto.
  • the p-doping material may be a material that has p-semiconductor properties, and one or two or more materials may be used.
  • the content of the p-doped material is 0 wt% to 50 wt% based on the compound of the formula (1).
  • the content of the p-doped material comprises 0 to 30% by weight based on the total solids content of the coating composition. In one embodiment of the present disclosure, the content of the p-doped material preferably comprises 1 to 30% by weight based on the total solid content of the coating composition, and in another embodiment, the p-doped material More preferably 10 to 30% by weight based on the total solids content of the coating composition.
  • the coating composition is a single molecule comprising a functional group that is crosslinkable by heat or light; Or a monomer capable of forming a polymer by heat.
  • a single molecule containing a functional group capable of crosslinking by heat or light as described above; Or a molecular weight of a monomolecule including an end group capable of forming a polymer by heat can be 3,000 g / mol or less.
  • the coating composition has a molecular weight of less than or equal to 2,000 g / mol and is a monolayer comprising a functional group capable of crosslinking by heat or light; Or a terminal molecule containing a terminal group capable of forming a polymer by heat.
  • the viscosity of the coating composition is from 2 cP to 15 cP.
  • the present disclosure also provides an organic light emitting device formed using the coating composition.
  • the organic material layer including the cured product of the coating composition is a hole transporting layer or a hole injecting layer.
  • the organic layer including the cured product of the coating composition is an electron transport layer or an electron injection layer.
  • the organic layer comprising the cured product of the coating composition is a light emitting layer.
  • the organic compound layer including the cured product of the coating composition is a light emitting layer, and the light emitting layer includes the compound of Formula 1 as a host of the light emitting layer.
  • the organic compound layer containing the coating composition is a light emitting layer, and the light emitting layer contains the compound of Formula 1 as a dopant of the light emitting layer.
  • the organic light emitting element is a hole injection layer, a hole transport layer, An electron transport layer, an electron injection layer, an electron blocking layer, and a hole blocking layer.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is an anode.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, one or more organic compound layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic layer, and an anode are sequentially stacked on a substrate.
  • 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer 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 layers.
  • FIG. 1 For example, the structure of an organic light emitting device according to one embodiment of the present specification is illustrated in FIG. 1
  • FIG. 1 shows an organic light emitting device in which an anode 201, a hole injecting layer 301, a hole transporting layer 401, a light emitting layer 501, an electron transporting layer 601 and a cathode 701 are sequentially stacked on a substrate 101 Are illustrated.
  • FIG. 1 illustrates an organic light emitting device and is not limited thereto.
  • the organic layers may be formed of the same material or different materials.
  • the organic light emitting device of the present invention can be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer is formed using a coating composition comprising the compound of Formula 1 above.
  • the organic light emitting device of the present specification can be manufactured by sequentially laminating an anode, an organic layer, and a cathode on a substrate.
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate by a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form an anode A hole injection layer, a hole transporting layer, a light emitting layer and an electron transporting layer, a deposition process, or the like, and then depositing a material usable as a cathode thereon.
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the present disclosure also provides a method of manufacturing an organic light emitting device formed using the coating composition.
  • a method comprising: preparing a substrate; Forming a first electrode on the substrate; Forming at least one organic layer on the first electrode; And forming a second electrode on the organic material layer, wherein forming the organic material layer includes forming at least one organic material layer using the coating composition.
  • the step of forming one or more organic layers using the coating composition uses a spin coating method.
  • the step of forming one or more organic layers using the coating composition uses a printing method.
  • the printing method includes, but is not limited to, ink jet printing, nozzle printing, offset printing, transfer printing, or screen printing.
  • the coating composition according to one embodiment of the present invention has a structural characteristic and is suitable for a solution process
  • the coating composition can be formed by a printing method, so that there is an economical effect in time and cost in manufacturing a device.
  • the step of forming one or more organic layers using the coating composition comprises: coating a coating composition on the first electrode; And heat treating or light treating the coated coating composition.
  • the heat treatment may be performed through heat treatment, and the heat treatment temperature in the heat treatment step may be 85 to 250 ° C, and may be 100 to 250 ° C according to an embodiment, In another embodiment, it may be between 150 ° C and 250 ° C.
  • the heat treatment time in the heat treatment step may be from 1 minute to 2 hours, and may be from 1 minute to 1 hour according to one embodiment. In another embodiment, 1 hour.
  • the organic compound layer formed using the coating composition includes the heat treatment or the light treatment step
  • the organic compound layer including a structure in which a plurality of the compounds included in the coating composition form a crosslink to form a thin film may be provided.
  • the organic compound layer formed using the coating composition includes the heat treatment or the light treatment step
  • the organic compound layer including a structure in which a plurality of the compounds included in the coating composition form a crosslink to form a thin film may be provided.
  • another layer is laminated on the surface of the organic material layer formed using the coating composition, it can be prevented that it is dissolved, morphologically affected or decomposed by the solvent.
  • the organic material layer formed using the coating composition is formed by including the heat treatment or the light treatment step, the resistance to the solvent is increased, so that the multilayer can be formed by repeating the solution deposition and crosslinking method, Life characteristics can be increased.
  • anode material a material having a large work function is preferably used so that injection of holes into the organic material layer is smooth.
  • the anode 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), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof.
  • Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO)
  • ZnO Al or SnO 2: a combination of a
  • the cathode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of the cathode material include metals such as barium, magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injecting layer is a layer for injecting holes from the electrode.
  • the hole injecting layer has a hole injecting effect for hole injecting effect on the anode, a hole injecting effect for the light emitting layer or the light emitting material due to its ability to transport holes to the hole injecting material,
  • a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • HOMO highest occupied molecular orbital
  • the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transport layer is a layer that transports holes from the hole injection layer to the light emitting layer and transports holes from the anode or the hole injection layer to the light emitting layer as the hole transport material.
  • the material is suitable. Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic compound.
  • Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • Examples of the dopant material include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • Specific examples of the aromatic amine derivatives include condensed aromatic ring derivatives having substituted or unsubstituted arylamino groups, and examples thereof include pyrene, anthracene, chrysene, and peripherrhene having an arylamino group.
  • styrylamine compound examples include substituted or unsubstituted Wherein at least one aryl vinyl group is substituted with at least one aryl vinyl group, and at least one substituent selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group is substituted or unsubstituted. Specific examples thereof include, but are not limited to, styrylamine, styryldiamine, styryltriamine, styryltetraamine, and the like.
  • the metal complex examples include iridium complex, platinum complex, and the like, but are not limited thereto.
  • the electron transporting layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Do. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
  • the electron injecting layer is a layer for injecting electrons from the electrode.
  • the electron injecting layer has an ability to transport electrons as an electron injecting material, has an electron injecting effect from the cathode, an excellent electron injecting effect to the light emitting layer or the light emitting material, A compound which prevents migration of excitons to the hole injection layer and is excellent in a thin film forming ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
  • the hole blocking layer is a layer which prevents the cathode from reaching the hole, and can be generally formed under the same conditions as the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.
  • the organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
  • the glass substrate on which ITO (indium tin oxide) was deposited to a thickness of 1500 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves. After the ITO was washed for 30 minutes, ultrasonic washing was repeated 10 times with distilled water twice. After the distilled water was washed, ultrasonic washing was performed with a solvent of isopropyl alcohol and acetone for 30 minutes each, and the substrate was transported to a glove box.
  • ITO indium tin oxide
  • the composition was cured. Thereafter, the layer was transferred to a vacuum evaporator, and then the following a-NPD was vacuum-deposited on the hole injection layer to form a hole transport layer.
  • a-NPD was deposited to a thickness of 40 nm, and the following Alq 3 was vacuum-deposited on the hole transport layer to form a light emitting layer.
  • Aluminum was deposited on the electron transport layer to a thickness of 0.5 nm and LiF to a thickness of 100 nm to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 A / sec, the LiF of the cathode was maintained at 0.3 A / sec, the deposition rate of aluminum was maintained at 2 A / sec, and the degree of vacuum during deposition was 2 x 10 -7 to 3 x 10 -5 torr.
  • An organic light emitting device was fabricated in the same manner as in Example 1 except that Compound 15 was used instead of Compound 1 in Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 28 was used instead of Compound 1 in Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 36 was used instead of Compound 1 in Example 1 and Compound E was used in place of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 51 was used instead of Compound 1 in Example 1 and Compound E was used in place of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 65 was used instead of Compound 1 in Example 1 and Compound E was used in place of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that the compound represented by Formula F was used instead of the compound represented by Formula D in Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 15 was used instead of Compound 1 in Example 1 and Compound (F) was used in place of Compound (D).
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 28 was used instead of Compound 1 in Example 1 and Compound (F) was used in place of Compound (D).
  • An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 36 was used instead of Compound 1 in Example 1 and Compound G was used in place of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 51 was used instead of Compound 1 in Example 1 and Compound G was used in place of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 65 was used instead of Compound 1 in Example 1, and Compound G was used instead of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1 except that the compound of Formula D was used instead of the compound of Formula D in Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 15 was used instead of Compound 1 in Example 1 and Compound H was used in place of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1 except that Compound 28 was used instead of Compound 1 in Example 1 and Compound H was used in place of Compound D in Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 36 was used instead of Compound 1 in Example 1 and Compound H was used instead of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 51 was used instead of Compound 1 in Example 1 and Compound H was used in place of Compound D in Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound 65 was used instead of Compound 1 in Example 1 and Compound H was used in place of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound V-1 was used in place of Compound 1 in Example 1, and Compound C was used in place of Compound D in Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound V-1 was used instead of Compound 1 in Example 1 and Compound G was used in place of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1, except that Compound V-1 was used instead of Compound 1 in Example 1 and Compound H was used instead of Compound D.
  • An organic light emitting device was prepared in the same manner as in Example 1 except that the following compound V-2 was used instead of the compound 1 in Example 1.
  • QE current efficiency and quantum efficiency
  • T90 90% of the initial luminance at the current density
  • Example 1 3.81 5.00 5.47 499.7 67.2
  • Example 2 3.85 5.15 5.43 515.6 65.1
  • Example 3 3.83 5.10 5.49 509.9 66.7
  • Example 4 3.83 5.11 5.57 510.7 70.8
  • Example 5 3.85 5.14 5.56 514.0 64.5
  • Example 6 3.82 5.05 5.44 498.0 65.1
  • Example 7 3.90 4.80 5.23 466.4 59.1
  • Example 8 3.87 5.00 5.41 505.5 65.0
  • Example 9 3.81 5.20 5.54 511.2 67.0
  • Example 10 3.90 4.75 4.92 455.1 55.7
  • Example 11 3.92 4.54 5.12 447.0 48.5
  • Example 12 3.98 4.60 5.01 464.1 57.9
  • Example 13 3.88 5.10 5.56 511.1 66.0
  • Example 14 3.90 4.88 5.31 470.3 65.9
  • Example 15 3.91 4.99 5.38 460.5 68.9
  • Example 16 3.93 5.21 5.60 513.4 71.1
  • Example 17 3.81 5.12 5.61

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Abstract

La présente invention concerne un composé représenté par la formule chimique (1), une composition de revêtement le comprenant, une diode électroluminescente organique l'utilisant et son procédé de préparation.
PCT/KR2018/010841 2017-09-26 2018-09-14 Composé, composition de revêtement le comprenant, diode électroluminescente organique l'utilisant, et son procédé de préparation Ceased WO2019066337A1 (fr)

Priority Applications (3)

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CN201880019908.3A CN110520407B (zh) 2017-09-26 2018-09-14 化合物、包含其的涂覆组合物、使用其的有机发光二极管和用于制备其的方法
US16/491,386 US11274213B2 (en) 2017-09-26 2018-09-14 Compound, coating composition comprising same, organic light-emitting diode using same, and method for preparing same
JP2019547493A JP6820057B2 (ja) 2017-09-26 2018-09-14 化合物、これを含むコーティング組成物、これを用いた有機発光素子およびその製造方法

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KR10-2017-0124472 2017-09-26
KR20170124472 2017-09-26
KR10-2018-0109385 2018-09-13
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