WO2019088751A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2019088751A1
WO2019088751A1 PCT/KR2018/013243 KR2018013243W WO2019088751A1 WO 2019088751 A1 WO2019088751 A1 WO 2019088751A1 KR 2018013243 W KR2018013243 W KR 2018013243W WO 2019088751 A1 WO2019088751 A1 WO 2019088751A1
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group
substituted
compound
unsubstituted
light emitting
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Korean (ko)
Inventor
윤홍식
이준엽
유지광
홍완표
김진주
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LG Chem Ltd
Sungkyunkwan University
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LG Chem Ltd
Sungkyunkwan University
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Priority claimed from KR1020180132914A external-priority patent/KR102072923B1/ko
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Priority to CN201880042006.1A priority Critical patent/CN110785416B/zh
Publication of WO2019088751A1 publication Critical patent/WO2019088751A1/fr
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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent materials, e.g. electroluminescent or chemiluminescent
    • C09K11/06—Luminescent materials, e.g. electroluminescent or chemiluminescent containing organic luminescent materials
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to a compound and an organic light emitting device including the same.
  • thermally activated delayed fluorescence is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission.
  • thermally activated delayed fluorescence is a phenomenon in which the inverse energy transfer from the excited triplet state to the excited singlet state is caused by thermal activation, leading to fluorescence emission.
  • the lifetime It is called delayed fluorescence in that long luminescence occurs. Since the retardation fluorescent material can use both fluorescence emission and phosphorescence emission, the problem of the cost of the phosphorescent material can be solved in that the problem of the external quantum efficiency of the conventional fluorescent material can be solved and the metal complex is not required.
  • the present invention provides a compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by the following formula (1).
  • X1 is O or S
  • Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted amine group; 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 halogen group; A nitrile group; A nitro group; A hydroxy group; Carbonyl group; An ester group; Imide; Amide group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted
  • r1 is an integer of 1 to 6
  • r2 and r3 are each an integer of 1 to 7,
  • r4 is an integer of 1 to 5
  • each of r1 to r4 is 2 or more, the structures in parentheses of 2 or more are equal to or different from each other.
  • a plasma display panel comprising a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.
  • the organic light emitting device including the compound represented by Chemical Formula 1 according to one embodiment of the present invention can improve the efficiency, improve the driving voltage and / or the lifetime characteristics.
  • FIG 1 shows an organic light emitting device according to an embodiment of the present invention.
  • the present invention provides a compound represented by the above formula (1).
  • the compound represented by Chemical Formula 1 includes a triazine group serving as an electron acceptor to facilitate electron injection, and the organic light emitting device including the compound has high efficiency and long life.
  • the compound represented by Formula 1 is separated with a triazine group acting as an electron acceptor and a biscarvazole acting as an electron pair between the linker, the retarded fluorescent property is enhanced and the organic light- Can be improved.
  • the compound represented by Formula 1 is a retardation fluorescent compound.
  • the number of excitons generated in the singlet and triplet is generated at a ratio of 25:75 (monomodal: triplet), and depending on the type of emission due to exciton migration, fluorescence emission, It can be divided into luminescence.
  • the phosphorescent light emission it means that the exciton of the excited state moves to the ground state and emits light.
  • the fluorescent emission the exciton of the excited state is in the ground state ground state, and the light is emitted.
  • the thermal activation delay fluorescent light emission is induced in the excited state from the excited state to the excited state, and the singlet excited state Means that the exciton moves to the ground state to cause fluorescent light emission.
  • the thermal activation delayed fluorescence emission is distinguished from fluorescence emission in that the peak position of the emission spectrum is the same as that of fluorescence but the decay time is long. The decay time is long, but the peak position of the emission spectrum differs from the phosphorescence spectrum and S 1 -T 1 < / RTI > energy difference.
  • S 1 is a singlet energy level
  • T 1 is a triplet energy level.
  • 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, , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted A halogen group; A nitrile group; A nitro group; Imide; Amide group; Carbonyl group; An ester group; A hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted alkylthio group; A substituted or unsubstituted arylthio group; A substituted or unsubstituted alkylsulfoxy group; A substituted or unsubstituted arylsulfoxy group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted boron group; A substituted or unsubstituted amine group; A
  • a substituent to which at least two substituents are connected 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 may be fluorine, chlorine, bromine or iodine.
  • the number of carbon atoms in the imide group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the amide group may be substituted with nitrogen of the amide group by hydrogen, a straight chain, branched chain or cyclic alkyl group of 1 to 30 carbon atoms or an aryl group of 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • the carbon number of the carbonyl group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specifically, it may be a compound having the following structure, but is not limited thereto.
  • the ester group may be substituted with an ester group oxygen in a straight chain, branched chain or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 30 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethyl-propyl, 1,1-dimethyl-propyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methyl
  • the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
  • the alkoxy group may be linear, branched or cyclic.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 30 carbon atoms. Specific examples include methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n Butyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like. But is not limited thereto.
  • the amine group is -NH 2 ; An alkylamine group; N-alkylarylamine groups; An arylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, and a heteroarylamine group, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, Phenylnaphthylenediamine group, N-phenylphenylenediamine group, N-phenyltriphenylamine group, N-phenylphenanthrenylamine group, N-phenylphenanthrenylamine group, Group, an N-phenanthrenylfluorenylamine group, and an N-biphenylfluorenylamine group, but the present invention is not limited thereto.
  • the N-alkylarylamine group means an amine group in which N of the amine group is substituted with an alkyl group and an aryl group.
  • the N-arylheteroarylamine group means an amine group in which N in the amine group is substituted with an aryl group and a heteroaryl group.
  • the N-alkylheteroarylamine group means an amine group in which N in the amine group is substituted with an alkyl group and a heteroaryl group.
  • the alkyl group in the alkylamine group, the N-arylalkylamine group, the alkylthio group, the alkylsulfoxy group and the N-alkylheteroarylamine group is the same as the alkyl group described above.
  • Specific examples of the alkyloxy group include a methylthio group, an ethylthio group, a tert-butylthio group, a hexylthio group and an octylthio group.
  • Examples of the alkylsulfoxy group include a mesyl group, an ethylsulfoxy group, a propylsulfoxy group, And the like, but the present invention is not limited thereto.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, Butenyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, (Diphenyl-1-yl) vinyl-1-yl, stilbenyl, stilenyl, and the like.
  • the alkynyl group may be straight-chain or branched, and the number of carbon atoms is not particularly limited, but is preferably from 2 to 30. Specific examples include but are not limited to ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, nonynyl, And the like, but the present invention is not limited thereto.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group,
  • the present invention is not limited thereto.
  • the boron group may be -BR 100 R 101 , wherein R 100 and R 101 are the same or different and each independently hydrogen; heavy hydrogen; halogen; A nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted, straight or branched chain alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • the phosphine oxide group specifically includes a diphenylphosphine oxide group, a dinaphthylphosphine oxide group, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but preferably has 6 to 30 carbon atoms, and the aryl group may be monocyclic or polycyclic.
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. And preferably 10 to 30 carbon atoms.
  • Specific examples of the polycyclic aryl group include naphthyl, anthracenyl, phenanthryl, triphenyl, pyrenyl, phenalenyl, perylenyl, , But is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent groups may combine with each other to form a ring.
  • adjacent means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom .
  • two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as " adjacent " groups to each other.
  • the aryl group in the aryloxy group, the arylthioxy group, the arylsulfoxy group, the N-arylalkylamine group, the N-arylheteroarylamine group and the arylphosphine group is the same as the aforementioned aryl group.
  • aryloxy group examples include a phenoxy group, a p-tolyloxy group, a m-tolyloxy group, a 3,5-dimethyl-phenoxy group, a 2,4,6- trimethylphenoxy group, a p- Naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group and 9-phenanthryloxy group and the arylthioxy group includes phenylthio group, 2- Methylphenylthio group, 4-tert-butylphenylthio group and the like, and examples of the arylsulfoxy group include a benzene sulfoxide group and a p-toluenesulfoxy group.
  • the present invention is not limited thereto.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, or a substituted or unsubstituted diarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group.
  • the arylamine group having at least two aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • the heteroaryl group includes at least one non-carbon atom and at least one hetero atom.
  • the hetero atom may include one or more atoms selected from the group consisting of O, N, Se and S, and the like.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 30 carbon atoms, and the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic group examples include a thiophene group, a furanyl group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a pyridyl group, a bipyridyl group, a pyrimidyl group, A substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic group, a substituted or unsubstituted heterocyclic
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, or a substituted or unsubstituted diheteroarylamine group.
  • the heteroarylamine group having two or more heteroaryl groups may include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group at the same time.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the above-mentioned heteroaryl group.
  • heteroaryl group in the N-arylheteroarylamine group and the N-alkylheteroarylamine group are the same as the examples of the above-mentioned heteroaryl group.
  • R 1 to R 4 are hydrogen.
  • the formula (1) is represented by the following formula (1-1).
  • X1, Ar1 and Ar2 are as defined in the above formula (1).
  • the formula (1) is represented by the following formula (1-2) or (1-3).
  • X1, Ar1 and Ar2 are as defined in the above formula (1).
  • 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.
  • Ar 1 and Ar 2 are the same or different and each independently represents an aryl group substituted or unsubstituted with an alkyl group; Or a heteroaryl group substituted or unsubstituted with an aryl group.
  • Ar1 and Ar2 are the same or different and are each independently a phenyl group; A biphenyl group; A fluorenyl group substituted or unsubstituted with an alkyl group; A dibenzofurane group; A dibenzothiophene group; Or a carbazolyl group substituted or unsubstituted with an aryl group.
  • Ar1 and Ar2 are the same or different and are each independently a phenyl group; A biphenyl group; A fluorenyl group substituted or unsubstituted with a methyl group; A dibenzofurane group; A dibenzothiophene group; Or a carbazolyl group substituted or unsubstituted with a phenyl group.
  • Formula 1 is selected from the following compounds.
  • the triplet energy level of the compound represented by Formula 1 is 2.1 eV or more, preferably 2.1 eV or more and 3.0 eV or less, 2.2 eV or more and 3.0 eV or less, 2.4 eV or more It can be less than 2.9 eV.
  • the triplet energy level of the compound represented by the formula (1) satisfies the above-mentioned range, the electron injection becomes easy and the formation ratio of the exciton increases, so that the luminous efficiency is increased.
  • ⁇ E st of the compound represented by Formula 1 is 0 eV to 0.3 eV, preferably 0 eV to 0.2 eV.
  • the ⁇ E st of the compound represented by Formula 1 is less than 0.2 eV.
  • E st means the difference between the singlet energy level (S 1 ) and the triplet energy level (T 1 ) of the compound represented by the formula ( 1 ).
  • a liquid crystal display comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes a compound represented by the general formula (1) .
  • the organic material layer of the organic light emitting device 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, an electron blocking layer, a light emitting layer, a hole blocking 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 fewer or more organic layers.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIG. 1, but is not limited thereto.
  • 1 illustrates a structure of an organic light emitting diode 10 in which a first electrode 30, a light emitting layer 40, and a second electrode 50 are sequentially stacked on a substrate 20.
  • 1 is an exemplary structure of an organic light emitting diode according to an embodiment of the present invention, and may further include another organic layer.
  • the organic layer includes a light emitting layer, and the light emitting layer includes a compound represented by the general formula (1).
  • the organic layer includes a light emitting layer
  • the light emitting layer includes the compound represented by the general formula (1) as a dopant of the light emitting layer.
  • the light emitting material of the light emitting layer is a material capable of emitting light in the visible light region by transporting and combining holes and electrons from the hole transporting layer and the electron transporting layer, At least one of the singlet energy and the triplet energies has a higher value than the light emitting material of the compound and has a hole transporting ability and an electron transporting ability and also has a long wavelength of light emission Can be prevented, and an organic compound having a high glass transition temperature can be included as a host.
  • the organic layer includes a light emitting layer, and the light emitting layer includes a host.
  • the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from a condensed aromatic ring derivative and a heterocyclic compound as a host of the light emitting layer.
  • the condensed aromatic ring derivative includes an anthracene derivative, a pyrene derivative, a naphthalene derivative, a pentacene derivative, a phenanthrene compound, a fluoranthene compound and the like.
  • the heterocyclic compound include carbazole derivatives , Dibenzofuran derivatives, ladder furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the host may include any one or more selected from the following compounds, but is not limited thereto.
  • the organic material layer includes a light emitting layer, and the light emitting layer contains the compound represented by the general formula (1) as a dopant of the light emitting layer, and at least one selected from a condensed aromatic ring derivative and a heterocyclic compound As a host of the light emitting layer.
  • the light emitting layer contains the dopant and the host in a weight ratio of 1:99 to 50:50.
  • the organic layer includes a light emitting layer, and the light emitting layer includes at least one selected from the group consisting of a dopant including the compound represented by the formula (1) and the condensed aromatic ring derivative and a heterocyclic compound Lt; / RTI > in a weight ratio of 1:99 to 50:50.
  • a dopant including the compound represented by the formula (1) and the condensed aromatic ring derivative and a heterocyclic compound Lt; / RTI > in a weight ratio of 1:99 to 50:50.
  • the organic layer includes a light emitting layer, and the light emitting layer may further include a fluorescent emitter.
  • the fluorescent layer includes the fluorescent emitter
  • the fluorescent emitter and the host are contained in a weight ratio of 0.5: 99.5 to 10: 90.
  • the fluorescent emitter can be an anthracene compound, a pyrene compound, a boron compound or the like, but is not limited thereto.
  • the organic luminescent device of the present invention includes the compound of the present specification as the dopant of the luminescent layer, that is, the compound represented by the above-mentioned formula (1), and is selected from the above-mentioned condensed aromatic ring derivative and the heterocyclic compound But may be made of materials and methods known in the art, except for including one or more of the foregoing.
  • 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 sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation Forming a first electrode, forming an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer, and an electron transporting layer on the first electrode, and depositing a material usable as a second electrode thereon.
  • PVD physical vapor deposition
  • an organic light emitting device can be formed by sequentially depositing a second electrode material, an organic material layer, and a first electrode material on a substrate.
  • the heterocyclic compound represented by Formula 1 may be formed into an organic layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is a cathode.
  • the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the cathode 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.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al, LiO 2 / Al, and Mg / Ag, but are not limited thereto.
  • the hole injecting layer is a layer for injecting holes from an electrode.
  • the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting 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.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • 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 electron transporting layer is a layer that receives electrons from the electron injecting 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.
  • suitable cathode materials are conventional materials with a low work function followed by an aluminum or silver layer, specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum or silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material.
  • a compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
  • Specific examples thereof include 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 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 process for preparing the material of the present invention begins with the reaction of synthesizing bromine and chlorine substituted dibenzofurane or dibenzothiophene as follows.
  • Dibenzofuran in which bromine and chlorine are substituted, or fluorine and chlorine are substituted.
  • the compounds of the specific examples were synthesized by introducing an epenergent triazine and a biscarbazole.
  • the compound represented by Formula 1 is incorporated into a light emitting layer together with a host material (m-CBP) having a triplet value of 2.5 eV or more to prepare an organic light emitting device, Respectively.
  • m-CBP host material having a triplet value of 2.5 eV or more
  • the glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water filtered by a filter of Millipore Co. was used as distilled water.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • hexanitrile hexaazatriphenylene (HAT) was thermally vacuum deposited on ITO to a thickness of 500 ⁇ to form a hole injection layer.
  • N-phenylamino] biphenyl 300 ⁇ was vacuum-deposited on the hole injection layer to form a hole transport layer, which is a material for transporting holes, and the following compound 4-4'-bis [N- (1-naphthyl) Respectively.
  • m-CBP and Compound 1 were vacuum deposited on the electron blocking layer to a thickness of 300 ANGSTROM at a weight ratio of 70:30 to form a light emitting layer.
  • Compound HB1 was vacuum deposited on the light emitting layer to a thickness of 100 ⁇ to form a hole blocking layer.
  • Compound ET1 and compound LiQ were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 ⁇ .
  • Lithium fluoride (LiF) and aluminum having a thickness of 2000 ⁇ were sequentially deposited on the electron injecting and transporting layer to form a cathode.
  • An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound shown in Table 1 was used instead of the compound 1 in Example 1.
  • An organic light emitting device was fabricated in the same manner as in Example 1, except that the compound of the following T1 to T4 and 4CzIPN was used instead of the compound 1 in Example 1.
  • Example 1 Compound 1 3.9 25 (0.33, 0.63)
  • Example 2 Compound 2 4.0 24 (0.34, 0.62)
  • Example 3 Compound 3 4.1 24 (0.33, 0.63)
  • Example 4 Compound 4 4.1 23 (0.33, 0.64)
  • Example 5 Compound 5 4.0 24 (0.33, 0.62)
  • Example 6 Compound 6 3.9 25 (0.32, 0.63)
  • Example 7 Compound 7 3.9 24 (0.33, 0.64)
  • Example 9 Compound 9 3.9 24 (0.33, 0.64) Comparative Example 1 T1 5.1 2 (0.25, 0.25) Comparative Example 2 T2 5.1 3 (0.29, 0.28) Comparative Example 3 T3 4.9 13 (0.34, 0.57) Comparative Example 4 T4 4.8 14 (0.33, 0.58) Comparative Example 5 4CzIPN 4.7 17
  • the measurement compound was dissolved in dimethylformamide (DMF) at a concentration of 5 mM and the electrolyte was measured at a concentration of 0.1 M, and oxidation and reduction potentials were determined by CV measurement. Respectively.
  • DMF dimethylformamide
  • T3, T4 and 4CzIPN correspond to retarded fluorescent compounds with ⁇ E st of less than 0.2 eV, but as shown in Table 1, compounds 1 to 9 exhibit better voltage and efficiency characteristics than T3, T4 and 4CzIPN there was.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé de formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2018/013243 2017-11-03 2018-11-02 Composé et dispositif électroluminescent organique le comprenant Ceased WO2019088751A1 (fr)

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KR1020180132914A KR102072923B1 (ko) 2017-11-03 2018-11-01 화합물 및 이를 포함하는 유기 발광 소자

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CN110885320A (zh) * 2019-10-31 2020-03-17 陕西莱特光电材料股份有限公司 叔胺化合物的制备方法
WO2021127381A1 (fr) * 2019-12-19 2021-06-24 Kyulux, Inc. Composition de substances destinée à être utilisée dans des diodes électroluminescentes organiques
CN113620848A (zh) * 2021-08-18 2021-11-09 苏州大学 一种硫酚与邻二碘苯的反应方法
CN113651738A (zh) * 2021-08-18 2021-11-16 苏州大学 一种苯硫醚化合物的制备方法

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KR20170039209A (ko) * 2014-07-29 2017-04-10 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
KR20170053590A (ko) * 2015-11-06 2017-05-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
WO2017115608A1 (fr) * 2015-12-28 2017-07-06 コニカミノルタ株式会社 COMPOSÉ π-CONJUGUÉ, MATÉRIAU D'ÉLÉMENT ÉLECTROLUMINESCENT ORGANIQUE, MATÉRIAU ÉLECTROLUMINESCENT, MATÉRIAU DE TRANSPORT DE CHARGE, COUCHE MINCE LUMINESCENTE, ÉLÉMENT ÉLECTROLUMINESCENT ORGANIQUE, DISPOSITIF D'AFFICHAGE ET DISPOSITIF D'ÉCLAIRAGE

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US20140158992A1 (en) * 2012-12-07 2014-06-12 Universal Display Corporation Carbazole Compounds For Delayed Fluorescence
US20150318487A1 (en) * 2014-05-02 2015-11-05 Samsung Display Co., Ltd. Organic light-emitting device
KR20170039209A (ko) * 2014-07-29 2017-04-10 메르크 파텐트 게엠베하 유기 전계발광 소자용 재료
KR20170013153A (ko) * 2015-07-27 2017-02-06 희성소재 (주) 유기 발광 소자 및 유기 발광 소자의 유기물층용 조성물
KR20170053590A (ko) * 2015-11-06 2017-05-16 희성소재 (주) 헤테로고리 화합물 및 이를 이용한 유기 발광 소자
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Cited By (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN110885320A (zh) * 2019-10-31 2020-03-17 陕西莱特光电材料股份有限公司 叔胺化合物的制备方法
WO2021127381A1 (fr) * 2019-12-19 2021-06-24 Kyulux, Inc. Composition de substances destinée à être utilisée dans des diodes électroluminescentes organiques
CN113620848A (zh) * 2021-08-18 2021-11-09 苏州大学 一种硫酚与邻二碘苯的反应方法
CN113651738A (zh) * 2021-08-18 2021-11-16 苏州大学 一种苯硫醚化合物的制备方法

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