WO2017138755A1 - 헤테로고리 화합물 및 이를 포함하는 유기전계발광소자 - Google Patents

헤테로고리 화합물 및 이를 포함하는 유기전계발광소자 Download PDF

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WO2017138755A1
WO2017138755A1 PCT/KR2017/001438 KR2017001438W WO2017138755A1 WO 2017138755 A1 WO2017138755 A1 WO 2017138755A1 KR 2017001438 W KR2017001438 W KR 2017001438W WO 2017138755 A1 WO2017138755 A1 WO 2017138755A1
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group
substituted
unsubstituted
divalent
heterocyclic compound
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French (fr)
Korean (ko)
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김민준
김공겸
권혁준
김정범
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주식회사 엘지화학
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Priority to JP2018538181A priority Critical patent/JP6825192B2/ja
Priority to CN201780010747.7A priority patent/CN108602836B/zh
Publication of WO2017138755A1 publication Critical patent/WO2017138755A1/ko

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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
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    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/12—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains three hetero rings
    • C07D487/14—Ortho-condensed systems
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D307/00—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom
    • C07D307/77—Heterocyclic compounds containing five-membered rings having one oxygen atom as the only ring hetero atom ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D307/91—Dibenzofurans; Hydrogenated dibenzofurans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
    • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D333/76—Dibenzothiophenes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
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    • 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
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L2924/00—Indexing scheme for arrangements or methods for connecting or disconnecting semiconductor or solid-state bodies as covered by H01L24/00
    • H01L2924/10—Details of semiconductor or other solid state devices to be connected
    • H01L2924/11—Device type
    • H01L2924/12—Passive devices, e.g. 2 terminal devices
    • H01L2924/1204—Optical Diode
    • H01L2924/12044—OLED
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present specification relates to a heterocyclic compound and an organic electroluminescent device including the same.
  • the electroluminescent device is a kind of self-luminous display device, and has an advantage of having a wide viewing angle, excellent contrast, and fast response speed.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from two electrodes are combined in the organic thin film to form a pair, then disappear and emit light.
  • the organic thin film may be composed of a single layer or multiple layers as necessary.
  • the material of the organic thin film may have a light emitting function as necessary.
  • a compound which may itself constitute a light emitting layer may be used, or a compound which may serve as a host or a dopant of a host-dopant-based light emitting layer may be used.
  • a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
  • the present specification provides a heterocyclic compound and an organic electroluminescent device including the same.
  • An exemplary embodiment of the present specification provides a heterocyclic compound represented by Formula 1 below.
  • Ar is a substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted arylamine group,
  • L is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • R1 to R15 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • Two or more adjacent groups of R1 to R4 may combine with each other to form a substituted or unsubstituted ring.
  • the present application is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the aforementioned heterocyclic compound. do.
  • the compound according to the exemplary embodiment of the present application may be used in an organic electroluminescent device to lower the driving voltage of the organic electroluminescent device, improve the light efficiency, and improve the life characteristics of the device by thermal stability of the compound.
  • FIG. 1 illustrates an example of an organic electroluminescent device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
  • FIG. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked. An example is shown.
  • FIG. 3 is an MS spectrum of Compound 1-17 according to Synthesis Example 2.
  • FIG. 4 is an MS spectrum of Compound 1-18 according to Synthesis Example 3.
  • FIG. 4 is an MS spectrum of Compound 1-18 according to Synthesis Example 3.
  • FIG. 5 is an MS spectrum of Compound 1-45 according to Synthesis Example 5.
  • FIG. 6 is an MS spectrum of Compound 4-45 according to Synthesis Example 9.
  • the present specification provides a heterocyclic compound represented by Chemical Formula 1.
  • substituted means that a hydrogen atom bonded to a carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where a substituent can be substituted, if two or more substituted , Two or more substituents may be the same or different from each other.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Alkyl groups; Cycloalkyl group; Alkenyl groups; An alkoxy group; Substituted or unsubstituted phosphine oxide group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 50.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n-pentyl , Isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl, n -Heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-o
  • the cycloalkyl group is not particularly limited, but preferably 3 to 60 carbon atoms, specifically, cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, cyclohexyl, 3-methylcyclohexyl, 4-methylcyclohexyl, 2,3-dimethylcyclohexyl, 3,4,5-trimethylcyclohexyl, 4-tert-butylcyclohexyl, cycloheptyl, cyclooctyl, and the like, but are not limited thereto. Do not.
  • the alkoxy group may be linear, branched or cyclic. Although carbon number of an alkoxy group is not specifically limited, It is preferable that it is C1-C20. Specifically, methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, isopentyloxy, n -Hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy, and the like. It is not limited.
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2- ( Naphthyl-1-yl) vinyl-1-yl, 2,2-bis (diphenyl-1-yl) vinyl-1-yl, stilbenyl group, styrenyl group and the like, but are not limited thereto.
  • phosphine oxide groups include, but are not limited to, diphenylphosphine oxide group, dinaphthylphosphine oxide, and the like.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but preferably 6 to 25 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • Carbon number is not particularly limited when the aryl group is a polycyclic aryl group. It is preferable that it is C10-24.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and adjacent substituents may be bonded to each other to form a ring.
  • the heterocyclic group includes one or more atoms other than carbon and heteroatoms, and specifically, the heteroatoms may include one or more atoms selected from the group consisting of O, N, Se, Si, and S, and the like. have.
  • carbon number of a heterocyclic group is not specifically limited, It is preferable that it is C2-C60.
  • heterocyclic group examples include thiophenyl group, furanyl group, pyrrole group, imidazolyl group, oxazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl group, acridil group, hydroacrylic Dill groups (e.g., ), Pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl, pyridopyrimidinyl, pyridopyrazinyl, pyrazinopyrazinyl, and isoquinolinyl , Indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, benzothiophenyl group, dibenzothiophenyl
  • the condensation structure may be a structure in which an aromatic carbon hydrogen ring is condensed to a corresponding substituent.
  • a condensed ring of benzimidazole Etc. but is not limited thereto.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 2 to 4.
  • Ra to Rl are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group.
  • Ra to Rl are hydrogen or deuterium.
  • Ra to Rl are hydrogen.
  • R1 to R4 are hydrogen or deuterium, or two or more adjacent groups combine with each other to form a benzene ring.
  • R1 to R4 are hydrogen, or two or more adjacent groups combine with each other to form a benzene ring.
  • R5 to R15 are hydrogen or deuterium.
  • R5 to R15 are hydrogen.
  • L is a direct bond; Substituted or unsubstituted phenylene group; Substituted or unsubstituted naphthalene group; A substituted or unsubstituted divalent triazine group; A substituted or unsubstituted divalent pyrimidine group; A substituted or unsubstituted divalent pyridine group; Substituted or unsubstituted divalent quinoline group; A substituted or unsubstituted divalent quinazoline group; A substituted or unsubstituted divalent benzoquinazolin group; A substituted or unsubstituted divalent quinolsaline group; A substituted or unsubstituted divalent pyridopyrimidine group; A substituted or unsubstituted divalent pyridopyrazine group; Substituted or unsubstituted divalent pteridine group; A substituted or unsubd
  • L is a direct bond; Phenylene group; Naphthalene group; Divalent pyridine group; Divalent quinoline groups; Divalent quinazoline group; Divalent benzoquinazolin group; Divalent quinolsaline group; Divalent pyridopyrimidine group; Divalent pyridopyrazine group; Divalent pteridine groups; Divalent pyrazinopyrazine groups; Divalent benzofurypyrimidine group; Divalent benzothienopimidine group; Or a divalent dimethyl indeno pyrimidine group.
  • L is a direct bond; Phenylene group; Naphthalene group; Divalent pyridine group; Divalent quinoline groups; Divalent quinazoline group; Divalent benzo [ h ] quinazolin group; Divalent benzo [ f ] quinazolin group; Divalent quinolsaline group; Divalent pyrido [3,2-d] pyrimidine groups; Divalent pyrido [2,3-d] pyrimidine groups; Divalent pyrido [2,3-b] pyrazine groups; Divalent pyrido [3,2-b] pyrazine groups; Divalent pteridine groups; Divalent pyrazino [2,3-b] pyrazine groups; Divalent benzofuro [3,2-d] pyrimidine group; Divalent benzothieno [3,2-d) pimidine group; Or a divalent dimethyl indeno [1,2-d] pyrimidine group.
  • Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzoquinazolin group; Substituted or unsubstituted phthalazine group; Substituted or unsubstituted isoquinoline group; Sub
  • Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzo [ f ] quinazoline group; Substituted or unsubstituted phthalazine group; Substituted or unsubstituted isoquino
  • Ar is a substituted or unsubstituted phenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dimethyl fluorenyl group; A substituted or unsubstituted bisbiphenylamine group; Substituted or unsubstituted triazine group; Substituted or unsubstituted pyrimidine group; Substituted or unsubstituted quinazoline group; Substituted or unsubstituted benzo [ f ] quinazoline group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted pyrido
  • the "substituted or unsubstituted" of Ar is deuterium; Halogen group; Cyano group; Nitro group; Hydroxyl group; Alkyl groups; Cycloalkyl group; Alkenyl groups; An alkoxy group; Substituted or unsubstituted phosphine oxide group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents of the substituents are connected, or does not have any substituents.
  • the "substituted or unsubstituted" of Ar is deuterium; Cyano group; Substituted or unsubstituted phosphine oxide group; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents of the substituents are connected, or does not have any substituents.
  • the "substituted or unsubstituted" of Ar is deuterium; Cyano group; Diphenyl phosphine oxide group; Phenyl group; Biphenyl group; Naphthyl group; Dibenzofuran group; And it is substituted with one or two or more substituents selected from the group consisting of dibenzothiophene group or substituted with a substituent to which two or more substituents of the substituent is connected, or means having no substituent.
  • the "substituted or unsubstituted" of Ar is deuterium; Phenyl group; Biphenyl group; Naphthyl group; Dibenzofuran group; And it is substituted with one or two or more substituents selected from the group consisting of dibenzothiophene group or substituted with a substituent to which two or more substituents of the substituent is connected, or means having no substituent.
  • the compound represented by Chemical Formula 1 is any one selected from the following structural formulas.
  • Formula 2A was prepared in the same manner as in Example 1, except that 1-bromo-2-chloronaphthalene was used instead of 1-bromo-2-chlorobenzene.
  • Formula 3A was prepared in the same manner as in Example 1, except that 2-bromo-3-chloronaphthalene was used instead of 1-bromo-2-chlorobenzene.
  • Formula 4A was prepared by the same method as the method of formula 1A of Preparation Example 1, except that 2-bromo-1-chloronaphthalene was used instead of 1-bromo-2-chlorobenzene.
  • the present specification provides an organic electroluminescent device comprising the compound described above.
  • the first electrode A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound.
  • the organic material layer of the organic electroluminescent device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic EL device may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer and the like as an organic material layer.
  • the structure of the organic electroluminescent device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound.
  • the thickness of the organic material layer is 1 kPa to 1000 kPa.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound as a host material.
  • the organic material layer includes a light emitting layer, the light emitting layer includes the heterocyclic compound, and further includes a dopant compound.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the heterocyclic compound and the dopant compound in a ratio of 100: 1 to 5: 5.
  • the dopant compound may be selected from the following structural formulas.
  • the organic material layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the heterocyclic compound.
  • the organic material layer includes an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer includes the heterocyclic compound.
  • the organic material layer includes an electron blocking layer or a hole blocking layer, and the electron blocking layer or the hole blocking layer includes the heterocyclic compound.
  • the organic electroluminescent device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode. Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers includes the heterocyclic compound.
  • the two or more organic material layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer simultaneously performing electron transport and electron injection, and a hole blocking layer.
  • the organic material layer includes two or more electron transport layers, and at least one of the two or more electron transport layers includes the heterocyclic compound.
  • the compound may be included in one layer of the two or more electron transport layers, and may be included in each of the two or more electron transport layers.
  • heterocyclic compound when the compound is included in each of the two or more electron transport layers, other materials except for the heterocyclic compound may be the same or different from each other.
  • the organic material layer further includes a hole injection layer or a hole transport layer including a compound including an arylamino group, carbazolyl group or benzocarbazolyl group in addition to the organic material layer including the heterocyclic compound.
  • the organic electroluminescent device may be an organic electroluminescent device having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic electroluminescent device may be an organic electroluminescent device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • FIGS. 1 and 2 For example, the structure of an organic EL device according to one embodiment of the present application is illustrated in FIGS. 1 and 2.
  • FIG. 1 illustrates a structure of an organic EL device in which a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 illustrates an organic electroluminescent device in which a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 3, an electron transport layer 7 and a cathode 4 are sequentially stacked.
  • the structure of is illustrated.
  • the compound may be included in at least one of the hole injection layer 5, the hole transport layer 6, the light emitting layer 3, and the electron transport layer 7.
  • the compound may be included in one or more layers of the hole injection layer, hole transport layer, light emitting layer and electron transport layer.
  • the organic EL device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present application, that is, the compound.
  • the organic material layers may be formed of the same material or different materials.
  • the organic EL device of the present application may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound, that is, the compound represented by Chemical Formula 1.
  • the organic EL device of the present application may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic EL device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the compound of Formula 1 may be formed of an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic EL device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic electroluminescent device may be fabricated by sequentially depositing an organic material layer and an anode material on a substrate (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc and gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), indium zinc oxide (IZO); ZnO: Al or SnO 2 : Combination of metals and oxides such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline, and the like, but are not limited thereto.
  • the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin, and lead or alloys thereof; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer.
  • the compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • the highest occupied molecular orbital (HOMO) of the hole injection material is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes 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 thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • 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 containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include compounds, dibenzofuran derivatives and ladder type furan compounds. , Pyrimidine derivatives, and the like, but is not limited thereto.
  • the electron transporting material 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 that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, nitrogen-containing five-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis (8-hydroxyquinolinato) zinc, bis (8-hydroxyquinolinato) copper, bis (8-hydroxyquinolinato) manganese, Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8-hydroxyquinolinato) gallium, bis (10-hydroxybenzo [h] Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the hole blocking layer is a layer for blocking the arrival of the cathode of the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes, and the like, but are not limited thereto.
  • the organic electroluminescent device may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 50 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • HT1 700 mW
  • HT2 200 mW
  • Compound 1-9 and dopant Dp-7 compound were vacuum deposited to a light emitting layer to a thickness of 300 kPa as a host.
  • the dopant was used in an amount of 3% by weight based on the total amount of the host and the dopant.
  • E1 compound 300 kPa was thermally vacuum deposited sequentially to the electron injection and transport layer.
  • An organic electroluminescent device was manufactured by depositing lithium fluoride (LiF) having a thickness of 12 kW and aluminum having a thickness of 2,000 kW sequentially on the electron transport layer to form a cathode.
  • LiF lithium fluoride
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • LiF was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 ⁇ / sec to 7 ⁇ / sec.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-17 was used instead of Compound 1-9 in Example 1.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-18 was used instead of Compound 1-9 in Example 1,
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 1-19 was used instead of Compound 1-9 in Example 1.
  • An organic electroluminescent device organic electroluminescent device organic electroluminescent device organic electroluminescent device group A compound instead of compound 1-9 in Example 1, except that compound 1-45 was used instead of compound 1-9 in Example 1
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that 4-9 was used.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 4-17 was used instead of Compound 1-9 in Example 1.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 4-19 was used instead of Compound 1-9 in Example 1.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that Compound 4-45 was used instead of Compound 1-9 in Example 1.
  • An organic light emitting diode device was manufactured according to the same method as Example 1 except for using H-1 instead of compound 1-9 in Example 1.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that H-2 was used instead of Compound 1-9 in Example 1.
  • An organic electroluminescent device was manufactured in the same manner as in Example 1, except that H-3 was used instead of Compound 1-9 in Example 1.
  • Table 1 shows the results of the organic electroluminescent devices produced according to Examples 1 to 9 and Comparative Examples 1 to 3. Voltage, efficiency and emission color are data at 5000 nit luminance. The lifetime was initially measured at 100% and the time at 98%.
  • the organic electroluminescent device using the compound of the present invention improved the luminous efficiency while lowering the driving voltage and all showed red light emission. It showed up to 80% more improvement in efficiency than H-1, a comparative material, and had the advantage of driving voltage as a whole.
  • Comparative Example 2 and Comparative Example 3 seemed to have the advantages of the driving voltage, the lifespan is less than half the level of Example 5, Comparative Example 1 is similar in life but did not seem to have a great advantage in terms of driving voltage and efficiency. Therefore, the compound of the present invention can be judged to have the advantages of high efficiency, low driving voltage and long life in the organic EL device.

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  • Chemical & Material Sciences (AREA)
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  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)
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  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
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US10249832B1 (en) 2017-12-06 2019-04-02 Idemitsu Kosan Co., Ltd. Organic electroluminescence device and novel compound
US10593889B1 (en) 2018-09-26 2020-03-17 Idemitsu Kosan Co., Ltd. Compound and organic electroluminescence device

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