WO2017043917A1 - Composé et diode électronique organique le comprenant - Google Patents

Composé et diode électronique organique le comprenant Download PDF

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WO2017043917A1
WO2017043917A1 PCT/KR2016/010170 KR2016010170W WO2017043917A1 WO 2017043917 A1 WO2017043917 A1 WO 2017043917A1 KR 2016010170 W KR2016010170 W KR 2016010170W WO 2017043917 A1 WO2017043917 A1 WO 2017043917A1
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substituted
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compound
experimental example
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곽지원
김진주
김성소
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주식회사 엘지화학
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Priority to CN201680022783.0A priority Critical patent/CN107531712B/zh
Publication of WO2017043917A1 publication Critical patent/WO2017043917A1/fr

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    • C—CHEMISTRY; METALLURGY
    • 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
    • C07D487/02—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 two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1011—Condensed systems
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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]

Definitions

  • the present specification relates to a compound and an organic electronic device including the same.
  • the organic electronic device refers to a device that requires charge exchange between an electrode and an organic material using holes and / or electrons.
  • the organic electronic device can be divided into two types according to the operating principle. First, excitons are formed in the organic material layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a form of electric element.
  • the second type is an electronic device in which holes and / or electrons are injected into an organic semiconductor forming an interface with the electrodes by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • Examples of the organic electronic device include an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), an organic transistor, and the like, all of which are used to inject or transport holes, inject or transport electrons, or light emitting materials to drive the device. need.
  • OPC organic photoconductor
  • the organic light emitting device will be described in detail.
  • a hole injection or transport material, an electron injection or transport material, or a light emitting material functions on a similar principle.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • organic light emitting devices When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
  • Such organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, high contrast, and high speed response.
  • the material used as the organic material layer in the organic light emitting device may be classified into a light emitting material and a charge transport material, such as a hole injection material, a hole transport material, an electron transport material, an electron injection material, and the like according to a function.
  • the light emitting materials may be classified into blue, green, and red light emitting materials, and yellow and orange light emitting materials required to achieve better natural colors, depending on the light emission color.
  • the maximum light emission wavelength is shifted to a long wavelength due to the intermolecular interaction, and the color purity decreases or the efficiency of the device decreases due to the light emission attenuation effect, thereby increasing color purity and energy transfer.
  • the host / dopant system can be used as a light emitting material.
  • the material constituting the organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
  • a stable and efficient material such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc.
  • the present specification is to provide a compound and an organic electronic device including the same.
  • Ar 1 is an unsubstituted aryl group
  • L is a substituted or unsubstituted arylene group
  • Ar 2 and Ar 3 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted carbazole group; Or a substituted or unsubstituted heteroaryl group containing at least one of N, O and S atoms,
  • R 1 , R 2 and R 7 to R 10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted amine group; Substitute
  • R 3 to R 6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group; Substituted or unsubstit
  • the present specification 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 compound of Formula 1. .
  • the compounds of the present disclosure may be used in organic layer devices such as hole injection materials, hole transport materials, light emitting materials, electron transport materials, electron injection materials, and the like, in particular as hole injection materials and / or hole transport materials. .
  • the driving voltage of the device may be lowered, the light efficiency may be improved, and the life characteristics of the device may be improved by thermal stability of the compound.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting device composed of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4. It is.
  • the compound represented by Chemical Formula 1 has an indolocarbazole ring structure as a core structure, thereby forming a thin film having high glass transition point and excellent heat resistance, and having high hole mobility and triplet. Energy levels and good electronic jersey can be expected.
  • 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.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of heterocyclic groups including one or more of N, O, S, Se, and Si atoms, or by connecting two or more substituents among
  • 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 and can be interpreted as a substituent to which two phenyl groups are linked.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • 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, i-propyloxy, n-butoxy, isobutoxy, tert-butoxy, sec-butoxy, n-pentyloxy, neopentyloxy, Isopentyloxy, n-hexyloxy, 3,3-dimethylbutyloxy, 2-ethylbutyloxy, n-octyloxy, n-nonyloxy, n-decyloxy, benzyloxy, p-methylbenzyloxy and the like It may be, but is not limited thereto.
  • the alkyl group may be linear or branched, and the 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-
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 30 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. It is not.
  • the alkenyl group may be linear or branched, and 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.
  • the silyl group is a substituent including Si and the Si atom is directly connected as a radical, represented by -SiR 104 R 105 R 106 , R 104 to R 106 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; An alkyl group; Alkenyl groups; An alkoxy group; Cycloalkyl group; Aryl group; And it may be a substituent consisting of at least one of a heterocyclic group.
  • silyl group examples include trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. It is not limited.
  • the boron group may be -BR 100 R 101 , wherein R 100 , and R 101 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted monocyclic or polycyclic cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted linear or branched alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted monocyclic or polycyclic aryl group having 6 to 30 carbon atoms; And it may be selected from the group consisting of a substituted or unsubstituted monocyclic or polycyclic heteroaryl group having 2 to 30 carbon atoms.
  • 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 30 carbon atoms.
  • the monocyclic aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl 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 heteroaryl group is a heterocyclic group containing one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heteroaryl groups include thiophene groups, furan groups, pyrrole groups, imidazole groups, thiazole groups, oxazole groups, oxadiazole groups, triazole groups, pyridyl groups, bipyridyl groups, pyrimidyl groups, triazine groups, triazole groups, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazo
  • adjacent group refers to a substituent substituted on an atom directly connected to an atom to which the corresponding substituent is substituted, a substituent positioned closest to the corresponding substituent stereoscopically, or another substituent substituted on an atom to which the substituent is substituted.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as “adjacent groups” to each other.
  • adjacent groups are bonded to each other to form a ring
  • the meaning that adjacent groups are bonded to each other to form a ring means that adjacent groups are bonded to each other, as described above, to form a 5 to 8 membered hydrocarbon ring or a 5 to 8 membered hetero ring.
  • Monocyclic or polycyclic and may be aliphatic, aromatic or condensed form thereof, but is not limited thereto.
  • the hydrocarbon ring may be an aromatic, aliphatic or a condensed ring of aromatic and aliphatic, and may be selected from examples of the cycloalkyl group or aryl group except for the above-mentioned monovalent one.
  • the amine group means a monovalent amine in which at least one hydrogen atom of the amino group (-NH 2 ) is substituted with another substituent, represented by -NR 107 R 108 , and R 107 and R 108 are the same as or different from each other.
  • substituents represented by -NR 107 R 108 , and R 107 and R 108 are the same as or different from each other.
  • -NH 2 Monoalkylamine groups; Dialkylamine groups; N-alkylarylamine group; Monoarylamine group; Diarylamine group; N-aryl heteroaryl amine group; It may be selected from the group consisting of N-alkylheteroarylamine group, monoheteroarylamine group and diheteroarylamine group, carbon number is not particularly limited, but is preferably 1 to 30.
  • Specific examples of the amine group include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group.
  • Diphenylamine group ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; N-biphenyl naphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; N-biphenylphenanthrenylamine group; N-phenyl fluorenyl amine group; N-phenylterphenylamine group; N-phenanthrenyl fluorenyl amine group; N-biphenyl fluorenylamine group and the like, but is not limited thereto.
  • the aryl group in the aryloxy group, arylthioxy group, aryl sulfoxy group, N-arylalkylamine group, N-arylheteroarylamine group, and arylphosphine group is the same as the examples of the aryl group described above.
  • the aryloxy group may be a phenoxy group, p-tolyloxy group, m-tolyloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-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, 9-phenanthryloxy group, and the like.
  • arylthioxy group examples include a phenylthioxy group and 2- The methylphenyl thioxy group, 4-tert- butylphenyl thioxy group, etc. are mentioned,
  • An aryl sulfoxy group includes a benzene sulfoxy group, p-toluene sulfoxy group, etc., but is not limited to this.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group, may be a polycyclic aryl group.
  • the arylamine group including two or more aryl groups may simultaneously include a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group.
  • the aryl group in the arylamine group may be selected from the examples of the aryl group described above.
  • arylamine group examples include phenylamine, naphthylamine, biphenylamine, anthracenylamine, 3-methyl-phenylamine, 4-methyl-naphthylamine, 2-methyl-biphenylamine, 9-methyl-anthra Cenylamine, diphenyl amine group, phenyl naphthyl amine group, ditolyl amine group, phenyl tolyl amine group, carbazole and triphenyl amine group and the like, but are not limited thereto.
  • examples of the heteroarylamine group include a substituted or unsubstituted monoheteroarylamine group, a substituted or unsubstituted diheteroarylamine group, or a substituted or unsubstituted triheteroarylamine group.
  • the heteroarylamine group including two or more heteroaryl groups may simultaneously include a monocyclic heteroaryl group, a polycyclic heteroaryl group, or a monocyclic heteroaryl group and a polycyclic heteroaryl group.
  • the heteroaryl group in the heteroarylamine group may be selected from the examples of the heteroaryl group described above.
  • the aromatic ring group may be monocyclic or polycyclic, and may be selected from examples of the aryl group except that it is not monovalent.
  • the divalent to tetravalent aromatic ring group may be monocyclic or polycyclic, meaning that the aryl group has 2 to 4 bonding positions, that is, 2 to 4 valent groups.
  • the description of the aforementioned aryl groups can be applied except that they are each 2 to 4 valent groups.
  • the arylene group refers to a divalent group having two bonding positions in the aryl group.
  • the description of the aforementioned aryl group can be applied except that they are each divalent.
  • the alkyl group among the aralkyl group, the alkylaryl group, and the alkylamine group may be applied to the description of the aforementioned alkyl group.
  • heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • alkenyl group of the alkenyl group may be applied to the description of the alkenyl group described above.
  • Ar 1 is an unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar 1 is an unsubstituted phenyl group, unsubstituted biphenyl group, unsubstituted terphenyl group, unsubstituted naphthyl group, unsubstituted anthracenyl group, unsubstituted phenanthryl group, non- It is a substituted pyrenyl group or an unsubstituted fluorenyl group.
  • Ar 1 is a phenyl group, a biphenyl group, or a naphthyl group.
  • Ar 1 is a phenyl group.
  • Ar 1 is a biphenyl group.
  • Ar 1 is a naphthyl group.
  • L is a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L is a substituted or unsubstituted phenylene group, a substituted or unsubstituted biphenylene group, a substituted or unsubstituted terphenylene group, a substituted or unsubstituted naphthylene group, a substituted or unsubstituted An anthracenylene group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenylene group, or a substituted or unsubstituted fluorenylene group.
  • L is a phenylene group, biphenylene group, terphenylene group, naphthylene group, anthracenylene group, phenanthryl group, pyrenylene group, or fluorenylene group.
  • L is a phenylene group, a biphenylene group, or a naphthylene group.
  • L is a phenylene group.
  • L is a biphenylene group.
  • L is a naphthylene group.
  • Ar 2 And Ar 3 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group, a substituted or unsubstituted cycloalkyl group, a substituted or unsubstituted aryl group, a substituted or unsubstituted alkenyl group, a substituted or unsubstituted carba Or a substituted or unsubstituted heteroaryl group containing one or more of N, O and S atoms.
  • Ar 2 And Ar 3 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar 2 And Ar 3 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group, a substituted or unsubstituted biphenyl group, a substituted or unsubstituted terphenyl group, a substituted or unsubstituted naphthyl group, a substituted or unsubstituted anthra A senyl group, a substituted or unsubstituted phenanthryl group, a substituted or unsubstituted pyrenyl group, or a substituted or unsubstituted fluorenyl group.
  • Ar 2 And Ar 3 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, anthracenyl group, a phenanthryl group, a pyrenyl group, or a fluorenyl group.
  • Ar 2 And Ar 3 are the same as or different from each other, and are each independently a phenyl group, a biphenyl group, a terphenyl group, or a naphthyl group.
  • Ar 2 And Ar 3 are the same as or different from each other, and are each independently a phenyl group.
  • Ar 2 And Ar 3 is the same as or different from each other, each independently, a biphenyl group.
  • Ar 2 And Ar 3 are the same as or different from each other, and are each independently a naphthyl group.
  • Ar 2 And Ar 3 are the same as or different from each other, and are each independently a terphenyl group.
  • R 1 , R 2 And R 7 To R 10 They are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted or unsubsti
  • R 1 or R 2 is an amine group unsubstituted or substituted with an alkyl group, a cycloalkyl group, an aryl group, or a heteroaryl group including one or more of N, O and S atoms.
  • R 1 or R 2 is an amine group substituted with a phenyl group, biphenyl group, terphenyl group, naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group or fluorenyl group.
  • R 1 , R 2 and R 7 to R 10 are hydrogen.
  • R 3 To R 6 They are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted phosphine oxide group; Substituted or unsubstituted aryl group
  • R 3 To R 6 They are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
  • R 3 To R 6 They are the same as or different from each other, and each independently a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, anthracenyl group, a phenanthryl group, a pyrenyl group, or a fluorenyl group to be.
  • R 3 to R 6 it is hydrogen.
  • the compound represented by Formula 1 is represented by any one of the following compounds.
  • the present specification provides an organic electronic 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 electronic device may be selected from the group consisting of an organic light emitting device, an organic solar cell, an organic photoconductor (OPC), and a glass transistor.
  • OPC organic photoconductor
  • the organic material layer of the organic electronic device of the present specification may have a single layer structure, but may have a multi-layered structure in which two or more organic material layers are stacked.
  • the organic electronic device of the present specification may have a structure including a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer and an electron injection layer as an organic material layer.
  • the structure of the organic electronic device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes
  • the hole injection layer, the hole transport layer, or a layer for simultaneously injecting and transporting the hole is It includes a compound of formula (1).
  • the organic electronic device may be an organic electronic 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 electronic device may be an inverted type organic electronic device in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG. In such a structure, the compound may be included in the light emitting layer.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is.
  • the 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 material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 1-A.
  • n 1 is an integer of 1 or more
  • Ar 11 is a substituted or unsubstituted monovalent or higher benzofluorene group; Substituted or unsubstituted monovalent or higher fluoranthene group; A substituted or unsubstituted monovalent or higher pyrene group; Or a substituted or unsubstituted monovalent or higher chrysene group,
  • L 11 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Substituted or unsubstituted silyl group; Substituted or unsubstituted germanium group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heteroaryl group, or may combine with each other to form a substituted or unsubstituted ring,
  • n 1 is 2 or more
  • the structures in two or more parentheses are the same or different from each other.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1-A as a dopant of the light emitting layer.
  • L 11 is a direct bond.
  • n 1 is 2.
  • Ar 11 is a divalent pyrene group unsubstituted or substituted with deuterium, methyl, ethyl, isopropyl, or tert-butyl groups; Or a divalent chrysene group unsubstituted or substituted with deuterium, methyl, ethyl or tert-butyl groups.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or alkyl group It is a substituted aryl group.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a methyl group.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently a substituted or unsubstituted phenyl group; Substituted or unsubstituted biphenyl group; Or a substituted or unsubstituted terphenyl group.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or alkyl group It is a phenyl group.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or alkyl group It is a ring biphenyl group.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, ethyl group, isopropyl group, tert-butyl group, nitrile group or alkyl group It is a ring terphenyl group.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently represent a substituted or unsubstituted heteroaryl group having 6 to 30 carbon atoms.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, a silyl group substituted with an alkyl group or a phenyl group It is a substituted or unsubstituted heteroaryl group.
  • Ar 12 and Ar 13 are the same as or different from each other, and each independently a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, a silyl group substituted with an alkyl group or a phenyl group Substituted or unsubstituted dibenzofuran group.
  • Chemical Formula 1-A is represented by the following compound.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by the following Chemical Formula 2-A.
  • G 11 is 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group, 4-phenanthryl group, 9 -Phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 3-methyl-2-naphthyl group, 4-methyl -1-naphthyl group, or ego,
  • G 12 is phenyl, 1-naphthyl group, 2-naphthyl group, 1-anthryl group, 2-anthryl group, 9-anthryl group, 1-phenanthryl group, 2-phenanthryl group, 3-phenanthryl group , 4-phenanthryl group, 9-phenanthryl group, 1-naphthacenyl group, 2-naphthacenyl group, 9-naphthacenyl group, 1-pyrenyl group, 2-pyrenyl group, 4-pyrenyl group, 2-biphenyl Aryl group, 3-biphenylyl group, 4-biphenylyl group, p-terphenyl-4-yl group, p-terphenyl-3-yl group, p-terphenyl-2-yl group, m-terphenyl-4-yl group, m-terphenyl-3-yl group, m-terphenyl-2-yl group, o-tolyl
  • G 13 and G 14 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • g 12 is an integer of 1 to 5
  • g 13 and g 14 are each an integer of 1 to 4,
  • g 12 to g 14 are each 2 or more, the structures in the two or more parentheses are the same as or different from each other.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes a compound represented by Formula 2-A as a host of the light emitting layer.
  • G 11 is a 1-naphthyl group.
  • G 12 is a 2-naphthyl group.
  • Formula 2-A is represented by the following compound.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the heterocyclic compound of the present specification, that is, the compound represented by Chemical Formula 1 above. .
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate by using a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation.
  • PVD physical vapor deposition
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and a first electrode material on a substrate.
  • the compound represented by Chemical Formula 1 may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured 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
  • 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, Mg / Ag, and the like, but are not limited thereto.
  • the hole injection layer is a layer for injecting holes from the electrode, and has a capability of transporting holes to the hole injection material, and has a hole injection effect at the anode, an excellent hole injection effect to the light emitting layer or the light emitting material, and is produced in the light emitting layer
  • the compound which prevents the excitons from moving 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 electron blocking layer is a layer that can prevent the holes injected from the hole injection layer to enter the electron injection layer through the light emitting layer to improve the life and efficiency of the device, if necessary, using a known material using a known material and the electron It may be formed in a suitable portion between the injection layers.
  • the light emitting material of the light emitting layer 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, benzothiazole 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 hetero ring-containing compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • heterocyclic-containing compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material examples include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, and metal complexes.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material a material capable of injecting electrons well from the cathode and transferring them to the light emitting layer is suitable. Do. 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 that blocks the reaching 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 light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • the compound represented by Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • Compound C (7.17 g, 22.2 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -4 12.27 g of Compound 4 was prepared by reacting and purifying in the same manner as in Preparation Example 1, except that amine (10.55 g, 22.2 mmol) was used.
  • Compound C (7.17 g, 22.2 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -2 11.86 g of Compound 5 was prepared by reacting and purifying in the same manner as in Preparation Example 1, except that amine (10.55 g, 22.2 mmol) was used.
  • Compound C (7.17 g, 22.2 mmol) and N-([1,1'-biphenyl] -4-yl) -4'-bromo-N-phenyl- [1,1'-biphenyl] -4 12.10 g of Compound 6 was prepared by reacting and purifying in the same manner as in Preparation Example 1, except that amine (10.55 g, 22.2 mmol) was used.
  • Compound C (7.17 g, 22.2 mmol) and N, N'-di ([1,1'-biphenyl] -4-yl) -4'-bromo- [1,1'-biphenyl] -4 12.66 g of Compound 7 was prepared by reacting and purifying in the same manner as in Preparation Example 1, except that amine (12.23 g, 22.2 mmol) was used.
  • Compound C (7.17 g, 22.2 mmol) and N-([1,1'-biphenyl] -4-yl) -3'-bromo-N-phenyl- [1,1'-biphenyl] -4 11.12 g of Compound 8 was prepared by reacting and purifying in the same manner as in Preparation Example 1, except that amine (10.55 g, 22.2 mmol) was used.
  • Compound C (7.17 g, 22.2 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4'-bromo- [1,1'-biphenyl] -4- 10.88 g of Compound 9 was prepared by reacting and purifying in the same manner as in Preparation Example 1, except that the mixture of 1)-[1,1'-biphenyl] -3-amine (12.23 g, 22.2 mmol) was used.
  • Compound C (7.17 g, 22.2 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1 ': 3', 1 ' 10.32 g of Compound 10 was prepared by reacting and purifying in the same manner as in Preparation Example 1, except that '-terphenyl] -4'-amine (12.23 g, 22.2 mmol) was used.
  • Compound C (7.17 g, 22.2 mmol) and N-([1,1'-biphenyl] -3-yl) -N-([1,1'-biphenyl] -4-yl) -6-bro 11.41 g of Compound 16 was prepared by reacting and purifying in the same manner as in Preparation Example 1, except that Monaphthalen-2-amine (11.66 g, 22.2 mmol) was used.
  • Compound D (7.84 g, 19.21 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -4 11.11 g of Compound 22 was prepared by reacting and purifying in the same manner as in Preparation Example 19, except that amine (9.13 g, 19.21 mmol) was used.
  • Compound D (7.84 g, 19.21 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -2 10.75 g of Compound 23 was prepared by reacting and purifying in the same manner as in Preparation Example 19, except that amine (9.13 g, 19.21 mmol) was used.
  • Compound D (7.84 g, 19.21 mmol) and N-([1,1'-biphenyl] -4-yl) -4'-bromo-N-phenyl- [1,1'-biphenyl] -4 10.82 g of Compound 24 was prepared by reacting and purifying in the same manner as in Preparation Example 19, except that amine (9.13 g, 19.21 mmol) was used.
  • Compound D (7.84 g, 19.21 mmol) and N-([1,1'-biphenyl] -4-yl) -3'-bromo-N-phenyl- [1,1'-biphenyl] -4 10.19 g of Compound 25 was prepared by reacting and purifying in the same manner as in Preparation Example 19, except that amine (9.13 g, 19.21 mmol) was used.
  • Compound E (8.71 g, 22.79 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -4 12.22 g of Compound 35 was prepared by reacting and purifying in the same manner as in Preparation Example 32, except that amine (10.83 g, 22.79 mmol) was used.
  • Compound E (8.71 g, 22.79 mmol) and N-([1,1'-biphenyl] -4-yl) -N- (4-bromophenyl)-[1,1'-biphenyl] -2 12.31 g of Compound 36 was prepared by reacting and purifying in the same manner as in Preparation Example 32, except that amine (10.83 g, 22.79 mmol) was used.
  • Compound E (8.71 g, 22.79 mmol) and N-([1,1'-biphenyl] -4-yl) -4'-bromo-N-phenyl- [1,1'-biphenyl] -4 12.37 g of Compound 37 was prepared by reacting and purifying in the same manner as in Preparation Example 32, except that amine (10.83 g, 22.79 mmol) was used.
  • Compound E (8.71 g, 22.79 mmol) and N-([1,1'-biphenyl] -4-yl) -3'-bromo-N-phenyl- [1,1'-biphenyl] -4 12.19 g of Compound 38 was prepared by reacting and purifying in the same manner as in Preparation Example 32, except that amine (10.83 g, 22.79 mmol) was used.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • Compound 1 which is a material for transporting holes, was vacuum deposited on the hole injection layer to form a hole transport layer.
  • the light emitting layer was formed by vacuum depositing the following BH and BD in a weight ratio of 25: 1 on the electron blocking layer with a film thickness of 300 GPa.
  • the following compound ET1 and LiQ were vacuum deposited on the light emitting layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 300 Pa.
  • lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode.
  • the lithium fluoride of the cathode was 0.3 ⁇ / sec
  • aluminum is deposited at a rate of 2 ⁇ / sec
  • the organic light emitting device was manufactured by maintaining 7 to 5 ⁇ 10 ⁇ 6 torr.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 2 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 3 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 4 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 5 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 6 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 7 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 8 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 9 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 10 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 11 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 12 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 13 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 14 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 15 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 16 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 17 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 18 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 19 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 20 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 21 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 22 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 23 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 24 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 25 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 26 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 27 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 28 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 29 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 30 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 31 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 32 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 33 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 34 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 35 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 36 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 37 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 38 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 39 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 40 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 41 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 42 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 43 was used instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 44 was used instead of compound 1 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following HT 1 instead of the compound 1 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following HT 2 instead of the compound 1 in Experimental Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following HT 3 instead of compound 1 in Experimental Example 1-1.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Millipore Co. product was used as distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • hexanitrile hexaazatriphenylene (HAT) of the following formula was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • the following compound 1 (400 kV) was deposited under vacuum to transport holes thereon, and the host RH and the dopant RD were vacuum deposited to a thickness of 300 kPa as a light emitting layer.
  • LiF lithium fluoride
  • aluminum 12 ⁇ of lithium fluoride (LiF) and 2,000 ⁇ of aluminum were deposited on the electron transport layer to form a cathode, thereby manufacturing an organic light emitting device.
  • 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 to 7 ⁇ / sec.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 2 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 3 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 4 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 1-1, except that compound 5 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 6 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 7 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 8 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 9 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 10 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 11 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 12 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 13 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 14 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 15 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 16 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 17 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 18 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 19 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 20 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 21 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 22 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 23 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 24 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 25 was used instead of Compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 26 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 27 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 28 was used instead of Compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 29 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 30 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 31 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 32 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 33 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 34 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 35 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 36 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 37 was used instead of compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 38 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 39 was used instead of Compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 40 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 41 was used instead of Compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 42 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 2-1, except that Compound 43 was used instead of Compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that compound 44 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following HT 1 instead of the compound 1 in Experimental Example 2-1.
  • the organic light emitting device was manufactured by the same method as Experimental Example 2-1, except that HT 2 was used instead of compound 1 in Experimental Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following HT 3 instead of the compound 1 in Experimental Example 2-1.

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

Abstract

La présente invention porte sur un composé et sur une diode électronique organique le comprenant.
PCT/KR2016/010170 2015-09-10 2016-09-09 Composé et diode électronique organique le comprenant WO2017043917A1 (fr)

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KR20180125369A (ko) * 2017-05-15 2018-11-23 주식회사 엘지화학 유기 발광 소자
CN108440537B (zh) * 2018-04-18 2021-04-27 石家庄诚志永华显示材料有限公司 咔唑衍生物、包含该咔唑衍生物的材料和有机电致发光器件
CN113980026B (zh) * 2021-11-25 2024-03-29 上海钥熠电子科技有限公司 咔唑衍生物类胺化合物和包含其的有机电致发光器件

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KR20150070214A (ko) * 2012-10-18 2015-06-24 도레이 카부시키가이샤 벤즈인돌로카르바졸 유도체, 그것을 사용한 발광 소자 재료 및 발광 소자
KR20140084413A (ko) * 2012-12-26 2014-07-07 주식회사 두산 유기 화합물 및 이를 포함하는 유기 전계 발광 소자
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JP2021504356A (ja) * 2017-11-23 2021-02-15 メルク パテント ゲーエムベーハー 電子デバイス用材料
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US11832513B2 (en) 2017-11-23 2023-11-28 Merck Patent Gmbh Materials for electronic devices

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CN107531712B (zh) 2021-02-26
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TW201718593A (zh) 2017-06-01
KR20170031073A (ko) 2017-03-20
CN107531712A (zh) 2018-01-02

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