WO2017052212A1 - Composé et dispositif optoélectronique organique le comprenant - Google Patents

Composé et dispositif optoélectronique organique le comprenant Download PDF

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WO2017052212A1
WO2017052212A1 PCT/KR2016/010562 KR2016010562W WO2017052212A1 WO 2017052212 A1 WO2017052212 A1 WO 2017052212A1 KR 2016010562 W KR2016010562 W KR 2016010562W WO 2017052212 A1 WO2017052212 A1 WO 2017052212A1
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group
substituted
unsubstituted
compound
formula
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PCT/KR2016/010562
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Korean (ko)
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차용범
홍완표
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주식회사 엘지화학
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Priority claimed from KR1020160110164A external-priority patent/KR101905970B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to US15/760,447 priority Critical patent/US10903431B2/en
Priority to CN201680055676.8A priority patent/CN108055841B/zh
Priority to EP16848937.5A priority patent/EP3339293B1/fr
Priority to JP2018512276A priority patent/JP6614520B2/ja
Publication of WO2017052212A1 publication Critical patent/WO2017052212A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D401/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom
    • C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
    • C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present application relates to a compound and an organic electronic device including the same.
  • This application is subject to the Korean Patent Application No. 10-2015-0135898 filed with the Korean Patent Office on September 24, 2015 and the Korean Patent Application No. 10-2016-0110164 filed with the Korean Patent Office on August 29, 2016. Claims interests, the contents of which are incorporated in full.
  • 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.
  • Such organic light emitting diodes 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.
  • a material which constitutes 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 is supported by a stable and efficient material.
  • the present application is to provide a novel compound and an organic electronic device comprising the same.
  • the present application provides a compound represented by the following Chemical Formula 1.
  • L 1 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar 1 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted heterocyclic group; Substituted or unsubstituted amine group; Or a substituted or unsubstituted silyl group,
  • R 1 to R 4 and R 7 to R 10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxyl group; Nitro group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R 11 to R 14 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxyl group; Nitro group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a ring,
  • R 5 and R 6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxyl group; Nitro group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or combine with an adjacent group to form a ring.
  • the present application is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the aforementioned compound.
  • the compound according to an exemplary embodiment of the present application is used in an organic electric device including an organic light emitting device to lower the driving voltage of the organic electric device, improve the light efficiency, and improve the life characteristics of the device by the thermal stability of the compound have.
  • FIG. 1 illustrates an example of an organic light emitting 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 light emitting 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.
  • 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; Amine groups; Phosphoryl group; Aryl group; And it means that 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 exemplified above, or do 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, 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 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.
  • 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, thiazolyl group, oxazolyl group, oxadiazolyl group, triazolyl group, pyridyl group, bipyridyl group, pyrimidyl group, triazinyl Groups, acridil groups, hydroacridyl 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
  • 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.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, 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.
  • 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 R 5 and R 6 may be represented by Formula 2 in combination with each other.
  • L 2 is a substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar 2 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; A substituted or unsubstituted heteroring group or a substituted or unsubstituted silyl group,
  • R 15 to R 18 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxyl group; Nitro group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroring group, or combine with an adjacent group to form a ring.
  • * and ** in the formula 1 and 2 means a portion to bind, * and ** are bonded to different parts.
  • R 5 and R 6 of Formula 1 when R 5 and R 6 of Formula 1 are combined with * and ** of Formula 2, one-to-one correspondence is provided, and a corresponding position is not limited.
  • R 5 may bind to *
  • R 6 may bind to **
  • R 5 may bind to **
  • R 6 may bind to *.
  • Chemical Formula 2 may be represented by any one of Chemical Formulas 2-1 to 2-3.
  • R 15 to R 18 and R 20 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Hydroxyl group; Nitro group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkenyl group; Substituted or unsubstituted alkynyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • t is an integer of 0-4, and when t is an integer of 2 or more, some R ⁇ 20> is the same or different from each other.
  • Chemical Formula 1 is represented by the following Chemical Formula 3 or 4.
  • Chemical Formula 1 is represented by any one of the following Chemical Formulas 1-1, 1-2, 3-1, 3-2, 4-1, and 4-2.
  • L 1 is a substituted or unsubstituted phenylene group; A substituted or unsubstituted bivalent biphenyl group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted pyridylene group; Substituted or unsubstituted pyrimidylene group; Or a substituted or unsubstituted triazinylene group.
  • the R 6 is -L 3 -Ar 3 .
  • L 3 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar 3 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted silyl group.
  • the R 12 is -L 4 -Ar 4 ,
  • L 4 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted divalent heterocyclic group,
  • Ar 4 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted silyl group.
  • L 4 is a direct bond; Phenylene group; Divalent biphenyl group; Pyridylene group; Pyrimidylene group; Or a triazinylene group.
  • Ar 4 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted amine group; Substituted or unsubstituted heterocyclic group; Or a substituted or unsubstituted silyl group.
  • Ar 4 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Ar 4 is hydrogen; heavy hydrogen; Halogen group; Cyano group; Methyl group; Phenyl group; Biphenyl group; Or a naphthyl group.
  • the Ar One To Ar 3 are the same as or different from each other, each independently represent a substituted or unsubstituted C 6 Through C 20 An aryl group; Substituted or unsubstituted C 2 Through C 20 A heterocyclic group; Or a substituted or unsubstituted amine group.
  • the aryl group is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted chrysenyl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluorenyl group.
  • the aryl group is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted chrysenyl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluorenyl group, wherein the substituted or unsubstituted deuterium; Halogen group; An alkyl group of C 1 to C 20 ; Cyano group; C 6 Through C 20 An aryl group; And it is substituted or unsubstituted fluorenyl group, wherein the substituted or unsub
  • the aryl group is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted chrysenyl group; Substituted or unsubstituted pyrenyl group; Substituted or unsubstituted triphenylenyl group; Or a substituted or unsubstituted fluorenyl group, wherein the substituted or unsubstituted deuterium; Halogen group; Methyl group; t-butyl group; Cyano group; Phenyl group; Biphenyl group; Naphthyl
  • the heterocyclic group is a substituted or unsubstituted pyridyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted triazinyl group; Substituted or unsubstituted thiophenyl group; Substituted or unsubstituted furanyl group; Substituted or unsubstituted benzofuranyl group; Substituted or unsubstituted benzothiophenyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Substituted or unsubstituted carbazolyl group; Substituted or unsubstituted benzocarbazolyl group; A substituted or unsubstituted dibenzocarbazolyl group; A substituted or unsubstituted dibenzocar
  • the heterocyclic group is a substituted or unsubstituted pyridyl group; Substituted or unsubstituted pyrimidyl group; Substituted or unsubstituted triazinyl group; Substituted or unsubstituted thiophenyl group; Substituted or unsubstituted furanyl group; Substituted or unsubstituted benzofuranyl group; Substituted or unsubstituted benzothiophenyl group; Substituted or unsubstituted dibenzofuranyl group; A substituted or unsubstituted dibenzothiophenyl group; Substituted or unsubstituted carbazolyl group; Substituted or unsubstituted benzocarbazolyl group; A substituted or unsubstituted dibenzocarbazolyl group; A substituted or unsubstituted dibenzocar
  • the amine group is represented by -NR'R ", wherein R 'and R" are the same as or different from each other, and each independently a substituted or unsubstituted C 1 to C 60 alkyl group; A substituted or unsubstituted C 6 to C 60 cycloalkyl group; Substituted or unsubstituted C 6 Through C 60 An aryl group; Or a substituted or unsubstituted C 2 Through C 60 It may be a heterocyclic group.
  • R 'and R " is a substituted or unsubstituted C 6 Through C 60
  • An aryl group, R' and R" may be the same or different from each other.
  • R 'and R " is a C 6 to C 60 aryl group unsubstituted or substituted with C 1 to C 60 Alkyl group, wherein R' and R" are the same as each other or Can be different.
  • the R 'and R are the same as or different from each other, and each independently may be a phenyl group, biphenyl group, naphthyl group, terphenyl group, fluorenyl group or dimethyl fluorenyl group.
  • the R One To R 4 And R 7 To R 10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; An alkyl group of C 1 to C 10 ; Or an aryl group of C 6 to C 20 .
  • the R One To R 4 And R 7 To R 10 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Methyl group; Or a phenyl group.
  • the R One To R 4 And R 7 To R 10 Is hydrogen.
  • the compound represented by Formula 1 is any one selected from structural formulas of the following Group 1.
  • the compound represented by Formula 1 is any one selected from the following structural formula of Group 2.
  • the compound represented by Formula 1 is any one selected from structural formulas of the following Group 3.
  • Compound according to an exemplary embodiment of the present application may be prepared by the production method described below.
  • the compound of Formula 1 may be prepared in the core structure as shown in Schemes 1 to 5.
  • Reaction Schemes 1 to 5 merely describe examples of the method of synthesizing the core of Chemical Formula 1, but are not limited thereto, and the type and position of the substituent may be changed as necessary.
  • Substituents may be combined by methods known in the art, and the type, position or number of substituents may be changed according to techniques known in the art. For example, substituents may be linked as shown in Schemes 6 and 7, but is not limited thereto.
  • the present disclosure provides an organic electronic device comprising the compound described above.
  • the first electrode A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein one or more layers of the organic material layers include the compound.
  • the organic material layer of the organic electronic device of the present application 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 light emitting 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 electronic device is not limited thereto and may include a smaller number of organic layers.
  • 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 an organic transistor.
  • OPC organic photoconductor
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the compound.
  • 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 compound.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the 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 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 compound.
  • the organic material layer includes an electron blocking layer
  • the electronic blocking layer includes the compound
  • the organic light emitting device is one or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer. It includes more.
  • the organic light emitting device includes 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 comprises the 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 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.
  • 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 compound.
  • the light emitting layer includes a compound of Formula 1 and further includes a light emitting dopant.
  • the light emitting dopant includes a phosphorescent dopant.
  • the phosphorescent dopant includes an iridium-based phosphorescent dopant.
  • the phosphor dopant material is Ir (ppy) 3 Or (piq) 2 Ir (acac).
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula A-1.
  • n1 is an integer of 1 or more
  • Ar5 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,
  • L5 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar6 and Ar7 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,
  • n1 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 A-1 as a dopant of the light emitting layer.
  • L5 is a direct bond.
  • n1 is 2.
  • Ar5 is a divalent pyrene group unsubstituted or substituted with deuterium, a methyl group, an ethyl group, or a tert-butyl group.
  • Ar6 and Ar7 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.
  • Ar6 and Ar7 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a germanium group substituted with an alkyl group.
  • Ar6 and Ar7 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a trimethylgermanium group.
  • Ar6 and Ar7 are the same as or different from each other, and each independently represent a substituted or unsubstituted phenyl group.
  • Ar6 and Ar7 is a phenyl group unsubstituted or substituted with a trimethylgermanium group.
  • the formula A-1 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 Chemical Formula A-2.
  • G11 is a phenyl group, 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,
  • G12 is a phenyl group, 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-biphenylyl 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
  • G13 and G14 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,
  • g12 is an integer of 1 to 5
  • g13 and g14 are each an integer of 1 to 4,
  • g12 to g14 are each two or more, the structures in two or more parentheses are the same as 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 A-2 as a host of the light emitting layer.
  • G11 is a phenyl group.
  • G11 is a 1-naphthyl group.
  • the G12 is a 2-naphthyl group.
  • the G13 and G14 is hydrogen.
  • the formula A-2 is represented by any one of the following compounds.
  • the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting diode may be an organic light emitting diode having 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 the structure of the organic light emitting device according to the exemplary embodiment of the present application is illustrated in FIGS. 1 and 2.
  • FIG. 1 illustrates a structure of an organic electronic 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 electronic 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 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 light emitting 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 light emitting 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 light emitting 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 light emitting 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 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 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 layer is a layer for injecting holes from an electrode.
  • the hole injection material has a capability of transporting holes to have a hole injection effect at an anode, and has an excellent hole injection effect for a light emitting layer or a light emitting material.
  • 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 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 transport layer is a layer that receives electrons from the electron injection layer and transports the electrons to the light emitting layer.
  • a material capable of injecting electrons well from the cathode and transferring the electrons to the light emitting layer is a material having high mobility to electrons. 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 light emitting device may be a top emission type, a bottom emission type, or a double-sided emission type according to a material used.
  • the compound may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the compound according to the present application may act on a principle similar to that applied to organic light emitting devices in organic electronic devices including organic solar cells, organic photoconductors, organic transistors, and the like.
  • formula A (10 g, 31.55 mmol) and 4-iodine-1,1'-biphenyl (9.72 g, 34.70 mmol) were completely dissolved in 180 ml of xylene, followed by sodium tert-butoxide (3.94 g). , 41.02 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.16 g, 0.32 mmol) was added thereto, and the mixture was heated and stirred for 2 hours.
  • Formula A (10 g, 31.55 mmol) and 4-bromo-N, N-diphenylaniline (11.21 g, 34.70 mmol) were completely dissolved in 200 ml of xylene, followed by sodium tert-butoxide (3.94 g, 41.02 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.16 g, 0.32 mmol) was added thereto, and the mixture was heated and stirred for 2 hours.
  • formula A (10 g, 31.55 mmol) and 3-bromo-9-phenyl-9H-carbazole (11.20 g, 34.70 mmol) were completely dissolved in 230 ml of xylene, followed by sodium tert-butoxide ( 3.94 g, 41.02 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.16 g, 0.32 mmol) was added thereto, and the mixture was heated and stirred for 4 hours.
  • Formula A (10 g, 31.55 mmol) and 9- (4-bromophenyl) -9H-carbazole (11.20 g, 34.70 mmol) were completely dissolved in 220 ml of xylene, followed by sodium tert-butoxide. (3.94 g, 41.02 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.16 g, 0.32 mmol) was added thereto, and the mixture was heated and stirred for 5 hours.
  • Formula A (10 g, 31.55 mmol), 2-chloro-4,6-diphenylpyrimidine (9.26 g, 34.70 mmol) were completely dissolved in 220 ml of xylene, followed by sodium tert-butoxide (3.94 g, 41.02 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.16 g, 0.32 mmol) was added thereto, and the mixture was heated and stirred for 3 hours.
  • formula A (10 g, 31.55 mmol) and 2-bromodibenzo [b, d] thiophene (9.09 g, 34.70 mmol) were completely dissolved in 190 ml of xylene, followed by sodium tert-butoxide (3.94 g, 41.02 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.16 g, 0.32 mmol) was added thereto, and the mixture was heated and stirred for 3 hours.
  • formula B (10 g, 27.25 mmol) and 4-bromo-N, N-diphenylaniline (9.59 g, 29.97 mmol) were completely dissolved in 180 ml of xylene, followed by sodium tert-butoxide (3.40 g, 35.43 mmol) was added, bis (tri- tert -butylphosphine) palladium (0) (0.14 g, 0.27 mmol) was added thereto, and the mixture was heated and stirred for 3 hours.
  • 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 was vacuum deposited to a film thickness of 100 kPa on the hole transport layer to form an electron blocking 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 compound ET1 and the compound LiQ were vacuum-deposited on the emission layer in a weight ratio of 1: 1 to form an electron injection and transport layer having a thickness of 300 kPa.
  • lithium fluoride (LiF) and aluminum were deposited to a thickness of 12 kPa in order to form a cathode.
  • 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.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the compound 5 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 compound 12 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 compound 13 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 compound 14 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.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1-1 except for using the following EB1 compound 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 EB2 compound 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 EB3 compound instead of compound 1 in Experimental Example 1-1.
  • the organic light emitting device manufactured by using the compound of the present invention as an electron blocking layer exhibits excellent characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 2-1 except for using the following compound of HT1 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 compound of HT2 instead of compound 1 in Experimental Example 2-1.
  • Comparative Example 2-1 and Comparative Example 2- in which a carbazole ring was formed in a direction different from that of the core of the present invention. It exhibits superior characteristics in terms of efficiency, driving voltage and / or stability of the organic light emitting device than the organic light emitting device manufactured by using the compound of 2 as the electron blocking layer.
  • 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.
  • the organic light emitting device was manufactured by the same method as Experimental Example 3, except that compound 6 was used instead of CBP in Experimental Example 3.
  • the organic light emitting device was manufactured by the same method as Experimental Example 3, except that compound 7 was used instead of compound CBP in Experimental Example 3.
  • the organic light emitting device was manufactured by the same method as Experimental Example 3, except that compound 8 was used instead of compound CBP in Experimental Example 3.
  • the organic light emitting device was manufactured by the same method as Experimental Example 3, except that compound 9 was used instead of compound CBP in Experimental Example 3.
  • the organic light emitting device was manufactured by the same method as Experimental Example 3, except that compound 10 was used instead of compound CBP in Experimental Example 3.
  • the organic light emitting device was manufactured by the same method as Experimental Example 3, except that compound 11 was used instead of compound CBP in Experimental Example 3.
  • the green organic light emitting device of Experimental Examples 3-1 to 3-6 using the compound represented by the present invention as a host material of the light emitting layer was prepared according to Experimental Example 3 (Comparative Example 3-1) using conventional CBP. It was confirmed that the green organic light emitting device showed better performance in terms of current efficiency and driving voltage. It can be seen that the above compounds having triazine, pyrimidine, pyridine, quinazoline as substituents as substituents are suitable as green light emitting organic devices.
  • the light emitting area of the ITO glass was patterned to have a size of 2 mm ⁇ 2 mm and then washed.
  • the substrate was mounted in a vacuum chamber and the base pressure was 1 ⁇ 10 ⁇ 6 torr.
  • the organic material was placed on the ITO as DNTPD (700), ⁇ -NPB (300 ⁇ s), and Compound 6 prepared according to the present invention as a host. (90 wt%), co-deposited (piq) 2 Ir (acac) (10 wt%) as a dopant (300 kPa), Alq 3 (350 kPa), LiF (5 kPa), Al (1,000
  • the film was formed in the order of iv) and measured at 0.4 mA.
  • the organic light emitting device for Comparative Example 4-1 was manufactured in the same manner except for using CBP, which is widely used as a general phosphorescent host material, instead of the organic light emitting compound prepared by the present invention as a host of the light emitting layer in the device structure of the above embodiment. .
  • T95 means the time taken for the luminance to be reduced to 95% from the initial luminance (5000 nits).

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Abstract

La présente invention concerne un composé et un dispositif optoélectronique organique le comprenant.
PCT/KR2016/010562 2015-09-24 2016-09-22 Composé et dispositif optoélectronique organique le comprenant WO2017052212A1 (fr)

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CN201680055676.8A CN108055841B (zh) 2015-09-24 2016-09-22 化合物和包含其的有机电子器件
EP16848937.5A EP3339293B1 (fr) 2015-09-24 2016-09-22 Composé et dispositif optoélectronique organique le comprenant
JP2018512276A JP6614520B2 (ja) 2015-09-24 2016-09-22 化合物およびこれを含む有機電子素子

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WO2018034242A1 (fr) * 2016-08-19 2018-02-22 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
WO2019101719A1 (fr) * 2017-11-23 2019-05-31 Merck Patent Gmbh Matériaux pour dispositifs électroniques
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