WO2017034239A1 - 화합물 및 이를 포함하는 유기 전자 소자 - Google Patents

화합물 및 이를 포함하는 유기 전자 소자 Download PDF

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WO2017034239A1
WO2017034239A1 PCT/KR2016/009192 KR2016009192W WO2017034239A1 WO 2017034239 A1 WO2017034239 A1 WO 2017034239A1 KR 2016009192 W KR2016009192 W KR 2016009192W WO 2017034239 A1 WO2017034239 A1 WO 2017034239A1
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group
substituted
unsubstituted
compound
layer
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PCT/KR2016/009192
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English (en)
French (fr)
Korean (ko)
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정민우
이동훈
허정오
허동욱
한미연
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주식회사 엘지화학
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Priority to CN201680023785.1A priority Critical patent/CN107531650B/zh
Publication of WO2017034239A1 publication Critical patent/WO2017034239A1/ko

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • 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
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
    • 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]
    • H10K50/17—Carrier injection layers
    • H10K50/171—Electron injection layers

Definitions

  • the present application relates to a compound and an organic electronic device including the same.
  • This application claims the benefit of the application date of Korean Patent Application No. 10-2015-0117897 filed with the Korea Intellectual Property Office on August 21, 2015, the contents of which are incorporated in full herein.
  • organic electronic device examples include an organic light emitting device.
  • 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.
  • the present application is to provide a compound and an organic electronic device comprising the same.
  • the present application provides a compound represented by the following Chemical Formula 1.
  • Z is C, Si or Ge
  • X 1 to X 3 are the same as or different from each other, at least one of X 1 to X 3 is N, and the rest are CR,
  • L is a direct bond; Substituted or unsubstituted arylene group; A substituted or unsubstituted divalent heterocyclic group; Or -NR'-,
  • R and R ' are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl group, a C 1 to C 40 alkyl group, a C 6 to C 40 cycloalkyl group A cycloalkyl group unsubstituted or substituted with at least one selected from the group consisting of C 6 to C 40 aryl groups, and C 2 to C 40 heterocyclic groups; Deuterium, halogen, cyano, nitro, substituted or unsubstituted silyl group, C 6 to C 40 cycloalkyl group, C 6 to C 40 aryl group, and C 2 to C 40 heterocyclic group An aryl group unsubstituted or substituted with at least one selected; Or deuterium, a halogen group, a cyano group, a nitro group, a substituted or unsubstituted silyl
  • R 1 to R 4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group of C 1 to C 10 ; Or an aryl group of C 6 to C 12 ,
  • n is an integer of 0 to 4, when n is an integer of 2 or more, a plurality of L are the same or different from each other,
  • p is an integer of 0 to 4, when p is an integer of 2 or more, a plurality of R 1 are the same as or different from each other,
  • q, r and s are each an integer of 0 to 5, and when q, r and s are each an integer of 2 or more, a plurality of R 2 to R 4 are the same or different from each other.
  • the present application is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.
  • the compound according to the exemplary embodiment of the present application may be used in organic electronic devices including organic light emitting devices, and may exhibit effects of low driving voltage, high luminous efficiency, and / or long life.
  • FIG. 1 shows 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 shows 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; Alkenyl groups; An alkoxy group; Cycloalkyl group; Amine groups; Aryl group; And it means that it is substituted with one or two or more substituents selected from the group consisting of a heterocyclic group or substituted with a substituent to which two or more substituents in the above-described substituents are connected, or does not have any substituents.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group 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 alkyl group may be linear or branched, carbon number is not particularly limited, but is preferably 1 to 50, more preferably 1 to 40.
  • 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,
  • 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 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 cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and more preferably 6 to 40 carbon atoms.
  • the aryl group is a monocyclic aryl group
  • carbon number is not particularly limited, but preferably 6 to 40 carbon atoms, and more 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, and S, and the like.
  • 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 Group, acridil group, pyridazinyl group, pyrazinyl group, quinolinyl group, quinazolinyl group, quinoxalinyl group, phthalazinyl group, pyridopyrimidinyl group, pyridopyrazinyl group, pyrazinopyrazinyl group, Isoquinolinyl group, indole group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, dibenzocarbazolyl group, be
  • 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 hydrocarbon ring or heterocycle herein may be selected from the examples of the cycloalkyl group, aryl group or heterocyclic group described above, except that they are monovalent, and may be monocyclic or polycyclic, aliphatic or aromatic or condensed form thereof. But. It is not limited only to these.
  • 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.
  • a divalent heterocyclic group refers to a divalent group having two bonding positions in the heterocyclic group.
  • the description of the aforementioned heterocyclic groups can be applied except that they are each divalent.
  • X 1 is N.
  • X 2 is N.
  • X 3 is N.
  • X 1 is CR.
  • X 2 is CR.
  • X 3 is CR.
  • X 1 and X 2 is N.
  • X 1 And X 3 Is N.
  • X 2 And X 3 Is N.
  • X 1 to X 3 is N.
  • the L is a direct bond; Or a substituted or unsubstituted arylene group.
  • the L is a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylylene group; Substituted or unsubstituted naphthylene group; Substituted or unsubstituted anthracenylene group; A substituted or unsubstituted fluorenylene group; Substituted or unsubstituted phenanthrenylene group; Substituted or unsubstituted pyrenylene group; And it is selected from the group consisting of a substituted or unsubstituted chrysenylene group.
  • the L is a direct bond; Phenylene group; Biphenylylene group; Naphthylene group; Anthracenylene group; Fluorenylene group; Phenanthrenylene group; Pyrenylene groups; And chrysenylene groups.
  • the L is a direct bond; Or a substituted or unsubstituted phenylene group.
  • the L is a direct bond; Or a phenylene group.
  • the L is a direct bond; or to be.
  • the dotted line in the structural formula is a position bonded to the N-containing heterocycle and the benzene ring of the formula (1).
  • n 1 or 2.
  • n 3 L are the same or different from each other.
  • n is 4, four L are the same or different from each other.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently a substituted or unsubstituted C 6 to C 20 aryl group; Or a substituted or unsubstituted C 2 to C 20 heterocyclic group.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently deuterium, a halogen group, a cyano group, a nitro group, a trimethylsilyl group, a C 6 to C 40 cycloalkyl group, C A C 6 to C 20 aryl group unsubstituted or substituted with at least one selected from the group consisting of 6 to C 40 aryl groups, and C 2 to C 40 heterocyclic groups; Or deuterium, halogen group, cyano group, nitro group, trimethylsilyl group, C 1 to C 40 alkyl group, C 6 to C 40 cycloalkyl group, C 6 to C 40 aryl group, and C 2 to C 40 hetero C 2 to C 20 heterocyclic group which is unsubstituted or substituted with at least one selected from the group consisting of a cyclic group.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently deuterium, a halogen group, cyano group, nitro group, trimethylsilyl group, C 6 to C 20 aryl group, and A C 6 to C 20 aryl group which is unsubstituted or substituted with at least one selected from the group consisting of C 2 to C 20 heterocyclic groups; Or at least one selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, a trimethylsilyl group, a C 1 to C 20 alkyl group, a C 6 to C 20 aryl group, and a C 2 to C 20 heterocyclic group Substituted or unsubstituted C 2 Through C 20 It is a heterocyclic group.
  • Ar 1 and Ar 2 are the same as or different from each other, and each independently selected from the group consisting of deuterium, a halogen group, a cyano group, a nitro group, a trimethylsilyl group, a phenyl group, and a biphenyl group A C 6 to C 20 aryl group which is unsubstituted or substituted with at least one; Or substituted with at least one selected from the group consisting of deuterium, halogen, cyano, nitro, trimethylsilyl, methyl, ethyl, propyl, i-propyl, butyl, t-butyl, phenyl, and biphenyl groups Or an unsubstituted C 2 to C 20 heterocyclic group.
  • an aryl group is a phenyl group; Biphenyl group; Naphthyl group; Anthracenyl group; Phenanthrenyl group; Chrysenyl group; Pyrenyl group; Triphenylenyl group; Or a fluorenyl group.
  • the heterocyclic group of C 2 To C 20 A pyridyl group; Pyrimidyl groups; Triazinyl group; Thiophenyl group; Furanyl group; Benzofuranyl group; Benzothiophenyl group; Dibenzofuranyl group; Dibenzothiophenyl group; Carbazolyl group; Benzocarbazolyl group; Or a dibenzocarbazolyl group.
  • the R1 to R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Methyl or phenyl.
  • the R1 to R4 is hydrogen.
  • Z is C, and the compound of Formula 1 is symmetric.
  • the compound represented by Formula 1 is asymmetric.
  • Z is C, and the compound of Formula 1 is asymmetric.
  • Z is Si
  • the compound of Formula 1 is asymmetric.
  • Z is Si
  • the asymmetric compound has the effect of low driving voltage, high emission rate and long life.
  • the bonding position is meta or ortho. it means.
  • the compound represented by Formula 1 may be any one selected from the following structural formulas.
  • 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 material layer of the organic electronic device of the present application may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic 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 phosphorescent device, an organic solar cell, an organic photoconductor (OPC) and an organic transistor.
  • 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 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 light emitting device is a hole injection layer, a hole transport layer. It further comprises one or two or more layers selected from the group consisting of an electron transport layer, an electron injection layer, an electron blocking layer and a hole blocking layer.
  • the organic light emitting device comprises a first electrode; A second electrode provided to face the first electrode; And a light emitting layer provided between the first electrode and the second electrode.
  • Two or more organic material layers provided between the light emitting layer and the first electrode, or between the light emitting layer and the second electrode, wherein at least one of the two or more organic material layers 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, a carbazole group, or a benzocarbazole group in addition to the organic material layer including the compound.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound of Formula A-1.
  • n is an integer of 1 or more
  • Ar3 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 1 is a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • Ar4 and Ar5 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 alkyl group; Substituted or unsubstituted arylalkyl group; Or a substituted or unsubstituted heterocyclic group, or may combine with each other to form a substituted or unsubstituted ring,
  • 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.
  • L1 is a direct bond.
  • m is 2.
  • Ar3 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 group.
  • Ar3 is a divalent pyrene group unsubstituted or substituted with an alkyl group; Or a divalent chrysene group unsubstituted or substituted with an alkyl group.
  • Ar3 is a divalent pyrene group unsubstituted or substituted with an alkyl group.
  • Ar3 is a divalent pyrene group.
  • Ar4 and Ar5 are the same as or different from each other, each independently represent a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • Ar4 and Ar5 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with an alkyl group, a nitrile group, or a silyl group substituted with an alkyl group.
  • Ar4 and Ar5 are the same as or different from each other, and each independently substituted or unsubstituted with a silyl group substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, and an alkyl group It is an aryl group.
  • Ar4 and Ar5 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a silyl group substituted with an alkyl group.
  • Ar4 and Ar5 are the same as or different from each other, and each independently an aryl group unsubstituted or substituted with a trimethyl silyl group.
  • Ar4 and Ar5 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.
  • Ar4 and Ar5 are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group, an ethyl group, an isopropyl group, a tert-butyl group, a nitrile group, or a trimethylsilyl group.
  • Ar4 and Ar5 are the same as or different from each other, and each independently represent a phenyl group unsubstituted or substituted with a trimethylsilyl group.
  • Ar4 and Ar5 are the same as or different from each other, each independently represent a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • Ar4 and Ar5 are the same as or different from each other, and each independently substituted or unsubstituted with a methyl group, an ethyl group, a tert-butyl group, a nitrile group, a silyl group substituted with an alkyl group or a phenyl group It is an aryl group.
  • Ar4 and Ar5 are the same as or different from each other, and each independently substituted or unsubstituted with a methyl group, ethyl group, tert-butyl group, nitrile group, trimethylsilyl group or phenyl group to be.
  • the formula A-1 is selected from the following compounds.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula A-2.
  • Ar6 and Ar7 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group,
  • G1 to G8 are the same as or different from each other, and each independently hydrogen; Substituted or unsubstituted monocyclic aryl group; Or a substituted or unsubstituted polycyclic aryl group.
  • 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.
  • Ar6 and Ar7 are the same as or different from each other, and each independently a substituted or unsubstituted polycyclic aryl group.
  • Ar6 and Ar7 are the same as or different from each other, each independently represent a substituted or unsubstituted polycyclic aryl group having 10 to 30 carbon atoms.
  • Ar6 and Ar7 are the same as or different from each other, and each independently a substituted or unsubstituted naphthyl group.
  • Ar6 and Ar7 are the same as or different from each other, each independently represent a substituted or unsubstituted 1-naphthyl group.
  • Ar6 and Ar7 are 1-naphthyl group.
  • the G1 to G8 is hydrogen.
  • the formula A-2 is selected from the following compounds.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound represented by Formula A-1 as a dopant of the light emitting layer
  • the compound represented by Formula A-2 includes a host of the light emitting layer Include as.
  • 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 shows 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 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 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 side 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 phosphors, organic solar cells, organic photoconductors, organic transistors, and the like.
  • Reagent 1 (100.0 g, 250.45 mmol) was mixed with reagent 2 (70.0 g, 275.46 mmol) and potassium acetate (73.7 g, 751.26 mmol) in a nitrogen atmosphere, added to 1000 ml of dioxane and heated with stirring.
  • Bis (dibenzylideneacetone) palladium (4.3g, 7.51mmol) and tricyclohexylphosphine (4.2g, 15.03mmol) were added under reflux, and the mixture was heated and stirred for 24 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration.
  • Reagent 7-1 (16.2 g, 84.62 mmol) was added to 170 ml of anhydrous tetrahydrofuran and cooled to -78 ° C. Thereafter, n-butyllithium (40.6mL, 101.54mmol) was slowly added dropwise over 30 minutes while stirring, followed by reaction for 1 hour. After adding the reagent 7-2 in a solid state and the reaction for 1 hour and slowly warmed to room temperature it was reacted for 2 hours. After the reaction, water was poured to terminate the reaction, and then the water layer and the organic layer were separated. n-butyllithium was purchased from Aldrich, and reagents 7-1 and 7-2 were obtained from TCI.
  • Compound 7A (21.0 g, 56.61 mmol) was mixed with reagent 2 (15.8 g, 62.27 mmol) and potassium acetate (16.7 g, 169.83 mmol) in a nitrogen atmosphere, added to 300 ml of dioxane and heated with stirring.
  • Bis (dibenzylideneacetone) palladium (1.0g, 1.70mmol) and tricyclohexylphosphine (1.0g, 3.40mmol) were added under reflux, and the mixture was heated and stirred for 24 hours. After the reaction was completed, the temperature was lowered to room temperature, followed by filtration.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) having a thickness of 1000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After washing ITO for 30 minutes, ultrasonic washing was performed twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • HT1 400 kPa
  • the host H1 and the dopant D1 compound were vacuum deposited to a thickness of 300 kPa as a light emitting layer.
  • Compound 1 and LiQ (Lithium Quinolate) prepared in Synthesis Example 1 were vacuum-deposited on the emission layer in a weight ratio of 1: 1 to form an electron injection and transport layer at a thickness of 350 Pa.
  • An organic light emitting device was manufactured by sequentially depositing lithium fluoride (LiF) and aluminum at a thickness of 2,000 ⁇ on the electron injection and transport layer sequentially to form a cathode.
  • LiF lithium fluoride
  • 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.
  • An organic light-emitting device was manufactured in the same manner as in Experimental Example 1-1, except that Compound ET1 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 of Chemical Formula 1 below ET2 in Experimental Example 1-1.
  • the organic light emitting device manufactured by using the compound of the present specification as an electron transporting material showing excellent properties in terms of efficiency and stability when compared to the case of using the Comparative Examples 1 and 2 materials Able to know.

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