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WO2018190522A1 - Nouveau composé et dispositif électroluminescent organique le contenant - Google Patents

Nouveau composé et dispositif électroluminescent organique le contenant Download PDF

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Publication number
WO2018190522A1
WO2018190522A1 PCT/KR2018/002941 KR2018002941W WO2018190522A1 WO 2018190522 A1 WO2018190522 A1 WO 2018190522A1 KR 2018002941 W KR2018002941 W KR 2018002941W WO 2018190522 A1 WO2018190522 A1 WO 2018190522A1
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group
substituted
carbon atoms
unsubstituted
compound
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PCT/KR2018/002941
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English (en)
Korean (ko)
Inventor
양정훈
이동훈
허정오
장분재
강민영
허동욱
한미연
정민우
Original Assignee
주식회사 엘지화학
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Priority claimed from KR1020180027124A external-priority patent/KR102041398B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880005166.9A priority Critical patent/CN110099902B/zh
Publication of WO2018190522A1 publication Critical patent/WO2018190522A1/fr

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    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • 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
    • C07D401/14—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 three or more hetero rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed system contains two hetero rings
    • C07D471/04—Ortho-condensed systems
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/654—Aromatic compounds comprising a hetero atom comprising only nitrogen as heteroatom
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • Novel compound and organic light emitting device comprising the same
  • the present invention relates to a novel compound and an organic light emitting device comprising the same.
  • organic luminescence refers to a phenomenon that converts electrical energy into light energy using organic materials.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, and excellent researches have been conducted because of excellent luminance ⁇ driving voltage and response speed characteristics.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic layer between the anode and the cathode.
  • the organic layer is often made of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer.
  • An object of the present invention is a novel compound capable of improving efficiency and low driving voltage and lifetime and characteristics when used as a material of an organic layer of an organic light emitting device, and An organic light emitting device is provided.
  • the present invention provides a compound of formula
  • A is C6-C20 aryl unsubstituted or substituted with a cyano group or a diphenylphosphine oxide group; Fluorenyl unsubstituted or substituted with a cyano group; And it is selected from the group consisting of heteroaryl containing 2 to 9 carbon atoms containing at least one nitrogen atom (N)
  • Ar 2 is selected from the group consisting of functional groups of Formulas 2a to 2e.
  • Ar 3 to Ar 5 are each independently hydrogen; heavy hydrogen; Alkyl having 1 to 20 carbon atoms; Aryl having 6 to 20 carbon atoms; Or C2-C20 heteroaryl including one or more heteroatoms selected from the group consisting of 0, N, Si, and S; and ⁇ and L 2 are each independently a bond; Or substituted or unsubstituted phenylene
  • Ri and 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted alkyl having 1 to 60 carbon atoms; Substituted or unsubstituted haloalkyl having 1 to 60 carbon atoms; Substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; Substituted or unsubstituted haloalkoxy having 1 to 60 carbon atoms; Substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; Substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; Substituted or unsubstituted aryl having 6 to 60 carbon atoms; Substituted or unsubstituted aryloxy having 6 to 60 carbon atoms; Or substituted or unsubstituted 0, N. Heteroaryl having 2 to 20 carbon
  • a and b are each independently an integer of 0 to 3, and c is an integer of 0 or 1.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound of Formula 1.
  • the compound of formula 1 described above can be used as the material of the organic layer of the organic light emitting device.
  • efficiency, low driving voltage, and / or lifetime characteristics can be improved.
  • the compound represented by Chemical Formula 1 may be used as a light emitting, electron transport, or electron injection material.
  • FIG. 1 shows a substrate 1, an anode 2, and a light emitting layer 3.
  • the example of the organic light emitting element which consists of the cathode 4 is shown.
  • FIG. 2 is a substrate (1).
  • An anode 2 a hole injection layer 5, a hole transport layer 6, a light emitting layer (7).
  • the example of the organic light emitting element which consists of the electron carrying layer 8 and the cathode 4 is shown. [Specific contents to carry out invention]
  • ⁇ means a bond connected to another substituent.
  • substituted or unsubstituted is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; "An aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl group; boron group; Alkyl group; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylaryl group; Haloalkyl; Haloalkoxy; Alkylamine group; Aralkyl amine groups; Heteroarylamine group; Arylamine group; Aryl phosphine group; Or substituted or unsubstituted with one or more substituents selected from the group consisting of a heterocyclic group including one or more hetero atoms selected from
  • the substituted or unsubstituted two or more substituents of the substituents exemplified above may be a biphenyl group.
  • the biphenyl group may be an aryl group. It can be interpreted as a substituent in which two phenyl groups are linked.
  • Carbon number of the carbonyl group in the present specification is not particularly limited, but carbon number 1 It is preferable that it is 40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the hydrogen of the carboxyl group may be substituted with a linear, branched or cyclic alkyl group having 1 to 25 carbon atoms or an aryl group having 6 to 25 carbon atoms. Specifically. It may be a compound of the following structural formula, but is not limited thereto.
  • the carbon number of the imide group is not particularly limited. It is preferable that it is C1-C25.
  • the compound may be of the structure
  • the silyl group is specifically trimethylsilyl group. Triethylsilyl group. t-butyldimethylsilyl group. Vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group. Diphenylsilyl group and phenylsilyl group and the like, but is not limited thereto.
  • the boron group is specifically trimethylboron group. Triethylboron group, t-butyldimethylboron group, triphenylboron group, phenylboron group and the like, but is not limited thereto.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be straight or branched chain, carbon number is not particularly limited, but is preferably 1 to 40. According to an exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms. Specific examples of the alkyl group include. Methyl, ethyl, propyl, n-propyl, isopropyl.
  • the alkenyl group may be linear or branched, and the carbon number is not particularly limited, but is preferably 2 to 40. According to one embodiment. Carbon number of the said alkenyl group is 2-20. According to another embodiment. Carbon number of the said alkenyl group is 2-10. According to another exemplary embodiment, the carbon number of the alkenyl group is. 2 to 6. Specific examples include vinyl, 1-propenyl. Isopropenyl, 1-butenyl. 2—butenyl, 3 one butenyl, 1 one pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1-butenyl. 1, 3-butadienyl. Allyl, 1-phenylvinyl— 1-yl,
  • cycloalkyl group is not particularly limited. Carbon number
  • Carbon number of the said cycloalkyl group is 3-30.
  • the cycloalkyl group has 3 to 20 carbon atoms.
  • the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl. Cyclobutyl, cyclopentyl, 3-methylcyclopentyl. 2.3-dimethylcyclopentyl, cyclonuclear chamber, 3- Methylcyclonuclear chamber. 4-methylcyclonuclear chamber, 2, 3-dimethylcyclonuclear chamber, 3,4,5-trimethylcyclonuclear chamber, 4-tert-butylcyclonuclear chamber. Cycloheptyl. Cyclooctyl and the like, but is not limited thereto.
  • the ' aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms. It may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, etc. as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group a naphthyl group, anthracenyl group, a phenanthryl group, a pyrenyl group, a perrylenyl group, a krasenyl group. Fluorenyl group and the like. It is not limited to this.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the fluorenyl group is substituted
  • the heterocyclic group is a heteroaryl or heterocycloalkyl group containing one or more heteroatoms selected from the group consisting of 0, N, Si, and S as heterologous elements. Although carbon number is not specifically limited, It is preferable that it is C2-C60.
  • the heterocyclic group include thiophene group and furan group. Pyrrole. Imidazole group, thiazole group. Oxazole group oxadiazole group. Triazole. Pyridyl groups. Bipyridyl groups, pyrimidyl groups, triazine groups, acridil groups. Pyridazine. Pyrazinyl groups.
  • the aryl group in an aralkyl group, an aralkenyl group, an alkylaryl group, and an arylamine group is the same as the example of the aryl group mentioned above.
  • the alkyl group in the aralkyl group, alkylaryl group, and alkylamine group is the same as the example of the alkyl group mentioned above.
  • the heteroaryl of the heteroarylamine may be applied to the description of the aforementioned heterocyclic group.
  • the alkenyl group in the aralkenyl group is the same as the example of the alkenyl group described above.
  • the arylene is a divalent group
  • the description about the aryl group described above may be applied.
  • the heteroarylene is a divalent group
  • the description of the aforementioned heterocyclic group may be applied.
  • the hydrocarbon ring is not monovalent.
  • the above description about the aryl group or cycloalkyl group can be applied except that two substituents are formed by bonding.
  • the heterocyclic ring is not a monovalent group, and the description of the aforementioned heterocyclic group may be applied except that two substituents are formed by bonding.
  • the present invention provides a compound of formula
  • Ar 2 is selected from the group consisting of functional groups of Formulas 2a to 2e.
  • Ar 3 to Ar 5 represent hydrogen, each independently selected; Distillate; C1-C20; C6-C20 aryl; Or heteroaryl having 2 to 20 carbon atoms containing at least one hetero atom from the group consisting of 0, N, Si and S.
  • L ! And L 2 are each independently bonded; Or substituted or unsubstituted phenylene, Ri and R 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted alkyl having 1 to 60 carbon atoms; Substituted or unsubstituted haloalkyl having 1 to 60 carbon atoms; Substituted or unsubstituted alkoxy having 1 to 60 carbon atoms; Substituted or unsubstituted haloalkoxy having 1 to 60 carbon atoms; Substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; Substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; Substituted or unsubstituted aryl having 6 to 60 carbon atoms; Substituted or unsubstituted aryloxy having 6 to 60 carbon atom
  • a and b are each independently an integer of 0 to 3, and c is an integer of 0 or 1.
  • the compound of Formula 1 includes a substituted or unsubstituted biphenyl fluorenyl group as a central structure, and the functional groups of A and Ar 2 for each of the benzene ring moieties in the fluorenyl group are each L and Having an asymmetrical structure bonded through 2 , and having an symmetrical structure in which the same functional groups are bonded around the biphenylfluorenyl group, the electron transport ability through various combinations. Bandgap, energy level and thermal characteristics can be adjusted more easily.
  • the compound of Formula 1 may be one having a structure of any one of the following formula la to lc:
  • Xi and 3 ⁇ 4 are either -LrA and — L 2 — Ar 2 . They are not identical to each other,
  • An. Ar 2 , a and b are as defined above.
  • solubility and thermal properties of the compounds depend on the crystallinity of the molecules, when the more structural obstacles are large, the crystallinity of the molecules is lowered, the process solubility and thermal properties. Is improved. therefore.
  • -Li-Ar, and — Compound represented by the formula (1) where —L 2 —Ar 2 is substituted in a structurally hindered position, —L ⁇ A and ⁇ L 2 -Ar 2 is structural
  • the process solubility and thermal properties of the molecule is improved, thereby.
  • Compound represented by the formula (1) has a process advantage in the synthesis, and when used in an organic light emitting device, there is an advantage that the thermal properties are improved.
  • A is more specifically, phenyl, naphthalenyl ⁇ anthracenyl substituted or unsubstituted with a cyano group or a diphenylphosphine oxide group.
  • n are each independently an integer of 0 or 1.
  • Ar 2 may be any one of the functional groups of Formulas 2a to 2e, and in Formulas 2a to 2e.
  • Ar 3 to Ar 5 is more specifically.
  • Each may independently be selected from the group consisting of hydrogen, alkyl having 1 to 4 carbon atoms, and phenyl, and more specifically, may be selected from the group consisting of hydrogen, methyl and fe.yl.
  • a linking group and ' L 2 are each independently a bond; Or substituted or unsubstituted phenylene, and in the case of substituted phenylene, At least one hydrogen in phenylene is deuterium; halogen; Cyano; Nitro; Amino; Substituted or unsubstituted alkyl having 1 to 60 carbon atoms; Substituted or unsubstituted haloalkyl having 1 to 60 carbon atoms; Substituted or unsubstituted C1-C60 alkoxy; Substituted or unsubstituted haloalkoxy having 1 to 60 carbon atoms; Substituted or unsubstituted cycloalkyl having 3 to 60 carbon atoms; Substituted or unsubstituted alkenyl having 2 to 60 carbon atoms; Substituted or unsubstituted aryl having 6 to 60 carbon atoms; Substituted or
  • Aryloxy of 60 Or substituted or unsubstituted, which may be substituted with a heteroaryl having 2 to 60 carbon atoms containing at least one hetero atom selected from the group consisting of 0, N, Si and S.
  • L 2 are each independently a bond; Or unsubstituted phenylene.
  • L and L 2 are functional groups having a large size such as anthracene, there is a fear of a decrease in color purity due to light emission of the functional group skeleton itself.
  • two functional groups — — An and —L 2 —Ar 2 bonded to a biphenylfluorenyl group may have different structures.
  • L 2 may be different, or A and Ar 2 may be different. Or and L 2 .
  • Ar ⁇ Ar 2 may both have different structures. More specifically, Ar 2 and Ar 2 may have different structures. When the two functional groups bonded to the biphenyl fluorenyl group in this way have a different structure. Compared to the case of having the same structure, the electron transport ability. The bandgap energy level and thermal characteristics can be adjusted more easily.
  • Two phenyl groups bonded to a fluorenyl group may each be substituted one or more with a substituent and R 2, where: And 3 ⁇ 4 are as defined above. More specifically and R 2 are each independently hydrogen; heavy hydrogen; halogen; Cyano; Nitro; Alkyl having 1 to 20 carbon atoms; Or aryl having 6 to 20 carbon atoms. More specifically, Ri and 3 ⁇ 4 are each independently. Hydrogen. heavy hydrogen. Halogen, cyano. Nitro, methyl. Or phenyl. In addition.
  • the number of substitutions (a and b) of or 3 ⁇ 4 for each phenyl group is each independently 0 to , More specifically, 0 or 1.
  • the compound of Formula 1 includes a substituted or unsubstituted biphenyl fluorenyl group as a central structure, and the functional groups of An and Ar 2 for each of the benzene ring portions in the fluorenyl group are each represented by L 2 and L 2 . It has an asymmetric structure containing two functional groups bonded together. Furthermore, at least one of the two functional groups includes at least one functional group of a heterocyclic group containing a nitrogen atom, thereby active electron transport capacity. Bandgap. Energy level. It can show the effect of controlling thermal characteristics.
  • the organic light emitting device using the same has the same functional groups bonded to the benzene ring portions present on both sides of the fluorenyl group, and the biphenyl fluorenyl group is mainly used.
  • High efficiency compared to organic light-emitting device employing a compound having a symmetrical structure. It may have a low driving voltage, high brightness and long life.
  • the compound of Formula 1 is. It can be prepared by the same method as in Banung Formula 1.
  • X is a halogen group such as chloro or boromo.
  • Y is boronic acid. Boronic acid ester. Or a boron (B) -containing organic group such as boronic acid pinacol ester group.
  • R 2 , L 2 . An, Ar 2 . a and b are as defined above.
  • organoboron compound (II) is Organoboron compound (II) comprises a functional group of -L 2 -Ar 2 , while halide (III) comprises a functional group, and halide (III) is illustrated as including a functional group of -L 2 -Ar 2 It may also contain a functional group of -LrA.
  • the compound (I) of Formula 1 may be prepared by reacting the organoboron compound (II) with Suzuki coupling in the presence of the halide (III), a base and a palladium catalyst.
  • the base may be sodium carbonate, potassium carbonate, sodium hydroxide or potassium hydroxide, and the like
  • the palladium catalyst may be tetrakis- (triphenylphosphine) palmulum (Pcl (PPH 3 ) 4 ), paramalacetate, or the like. This can be used.
  • the reaction may be carried out in an organic solvent such as tetrahydrofuran (THF), NN-dimethylformamide (DMF), dimethyl sulfoxide (DMS0) or toluene.
  • THF tetrahydrofuran
  • DMF NN-dimethylformamide
  • DMS0 dimethyl sulfoxide
  • the Suzuki coupling reaction of the reaction formula 1 may be performed in the range of 80 ° C. to 120 ° C.
  • organoboron compound (II) may be prepared directly, or commercially It can also be obtained.
  • the organoboron compound ( ⁇ ) may be determined in kind depending on the positions of Li—Ar and L 2 —Ar 2 functional groups bonded to the biphenylfluorenyl group in the compound of Formula 1 to be finally prepared.
  • the compounds of the formulas la to lc of the present invention may be prepared using the organoboron compounds prepared in the same manner as in the schemes 2 to 4, respectively.
  • Reaction Schemes 2 to 4 are only examples for describing the present invention, but the present invention is not limited thereto.
  • NBS 11—bromosuccininiide
  • DMF dimethyl Formamide (Dimethyl Formami de)
  • THF tetrahydrofuran
  • AN acetonitrile
  • KOAc potassium acetate.
  • the compound of Formula 1 may be prepared by appropriately replacing the starting material in accordance with the structure of the compound to be prepared with reference to the reaction formula 1 to 4.
  • the present invention provides an organic light emitting device comprising the compound of Formula 1.
  • the present invention comprises 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 comprises a compound represented by Chemical Formula 1. do.
  • the organic material layer of the organic light emitting device of the present invention may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked. for example.
  • the organic light emitting device of the present invention is a hole injection layer, a hole transport layer as an organic material layer.
  • Light emitting layer It may have a structure including an electron transport layer, an electron injection layer and the like.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic layer a hole injection dancing. Hole transport layer. Or a layer for simultaneously injecting and transporting holes, wherein the hole injection layer. Hole transport layer. Alternatively, the layer for simultaneously injecting and transporting a hole may include a compound represented by Chemical Formula 1.
  • the organic layer may include a light emitting layer.
  • the light-emitting layer is, comprising a compound of the formula (1).
  • the organic layer is an electron transport layer. Or an electron injection layer.
  • the electron transport layer, or the electron injection insect comprises a compound represented by the formula (1).
  • the electron transport layer includes the compound represented by Chemical Formula 1.
  • the compound represented by Formula 1 according to the present invention has excellent thermal stability, high triplet energy (ET), and hole stability.
  • an n-type dopant used in the art may be mixed and used.
  • the organic material layer may include a light emitting layer and an electron transport layer, and the electron transport layer may include a compound represented by Chemical Formula 1.
  • the organic light emitting device may have a structure in which one or more organic material layers and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device according to the present invention may be an organic light emitting device of an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate. for example.
  • the structure of an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • FIG. 2 shows a substrate 1.
  • Anode (2) Hole injection layer (5).
  • the example of the organic light emitting element which consists of the electron carrying layer 8 and the cathode 4 is shown.
  • the compound represented by Formula 1 is the hole injection layer, a hole transport layer. It may be included in one or more layers of the light emitting layer and the electron transport layer.
  • An organic light emitting device may be prepared by materials and methods known in the art, except that the compound represented by Chemical Formula 1 is included. Also.
  • the organic light emitting device includes a plurality of organic material layers, the organic material layers may be formed of the same material or different materials.
  • An organic light emitting device is a first electrode on a substrate.
  • the organic material layer and the second electrode may be sequentially stacked. At this time.
  • PVD physical vapor deposition method
  • a metal or conductive metal oxide or an alloy thereof is deposited on a substrate to form an anode, and an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer is formed thereon, and then used as a cathode thereon. It can be prepared by depositing a material that can be. In addition to methods like this.
  • An anode material may be sequentially deposited to make an organic light emitting device.
  • the compound represented by Formula 1 may be used to prepare an organic light emitting device.
  • the organic layer may be formed by a solution coating method as well as a vacuum deposition method. here .
  • Solution coating refers to spin coating. Dip coating. Doctor Blading. Inkjet printing. Screen printing.
  • the spray method means coating, but is not limited to these. ⁇
  • An organic light emitting device may be manufactured by sequentially depositing an anode material (W0 2003/012890). However, the manufacturing method is not limited thereto.
  • the first electrode is an anode.
  • the second electrode is a cathode, or the first electrode is a cathode, and the second electrode is an anode
  • the anode material a material having a large work function is generally preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include vanadium, chromium and copper. Metals such as zinc or gold or alloys thereof; Zinc oxide. Indium oxide. Indium tin oxide ( ⁇ ). Metal oxides such as zinc oxide (IZ0); ⁇ : ⁇ 1 or SN0 2 : A combination of a metal and an oxide such as Sb; Poly (3-methylthiophene). Conductive polymers such as poly [3.4- (ethylene-1, 2-dioxy) thiophene] (PED0T), polypyrrole and polyaniline. It is not limited only to these.
  • the anode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material are magnetite. calcium. Sodium . . Kalm. Titanium, indium, yttrium. lithium. gadolinium. Aluminum, silver. Metals such as tin and lead or alloys thereof; multimodal structural materials such as LiF / Al or Li0 2 / Al. It is not limited only to these.
  • the hole injection material may be a charge for injecting holes from an electrode. As the hole injection material, it has the ability to transport holes.
  • the hole injection material has an excellent hole injection effect on the light emitting layer or the light emitting material, and prevents the excitons generated in the light emitting layer from moving to the electron injection layer or the electron injection material. Also. Compounds excellent in thin film formation ability are preferred. It is preferable that the HOMCX highest occupied molecul ar orbi ta) of the hole injection material is between the work function of the anode material and H0M0 of the surrounding organic layer.
  • the hole injection material include metal porphyr (porphyr in), oligothiophene, arylamine-based organic matter, nucleonitrile nucleated azatriphenylene-based organic material. Quinacridone (qui nacr i done) Organics. Of perylene series Organic materials, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer for receiving holes from the hole injection layer to transport holes to the light emitting layer.
  • a material for transporting holes from the anode or the hole injection layer to the hole transporting material a material having high mobility to holes is suitable. Specific examples include, but are not limited to, an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together.
  • 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 include 8-hydroxy-quinoline aluminum complex (Ak l3 ); Carbazole series compounds; Diiiier i zed styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Polymers of the poly (P-phenylenevinylene) (PPV) family; Spi ro compounds; Polyfluorene. Rubren, etc. It is not limited only to these.
  • 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 compounds include carbazole derivatives and dibenzofuran derivatives. Ladder type furan compounds, pyrimidine derivatives, and the like. It is not limited to this.
  • Dopant materials include aromatic amine derivatives. Strylamine compound, boron complex, fluoranthene compound. Metal complexes; Specifically, as an aromatic amine derivative, as a condensed aromatic ring derivative having a substituted or unsubstituted arylamino group, pyrene having an arylamino group. Anthracene, chrysene. Periplanten.
  • the styrylamine compound is a compound in which at least one arylvinyl group is substituted with a substituted or unsubstituted arylamine. Aryl group.
  • Substituents selected from one or two or more selected from the group consisting of silyl, alkyl, cycloalkyl and arylamino groups are substituted or unsubstituted. Specifically styrylamine , styryldiamine ⁇ Styryltriamine. Styryltetraamine and the like, but is not limited thereto.
  • a metal complex an iridium complex. There is a platinum complex. It is not limited to this.
  • the dopant content may be from 1% to 99% relative to the host amount of the light emitting layer.
  • the electron transporting material in the electron in layer receives an electron from the injection layer of transporting electrons to the electron transport material balgwangchung receives electrons from the cathode as a material that can move to the light-emitting "layer.
  • Materials with high mobility for the electron are suitable. Specific examples include Al complexes of 8—hydroxyquinoline; Complexes including A1; 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 according to 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 for injecting electrons from the electrode. Has the ability to transport electrons, the effect of electron injection from the cathode. It has an excellent electron injection effect with respect to a light emitting layer or a light emitting material, and prevents the movement of the excitons produced
  • the metal complex compound include 8-hydroxyquinolinato lithium lithium bis (8-hydroxytunolinato) zinc and bis (8-hydroxyquinolinato) copper.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the compound represented by Chemical Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • a glass substrate coated with a thin film having an indium tin oxide (IT0) of 1.000 A was placed in distilled water in which a detergent was dissolved, and ultrasonically cleaned.
  • Fischer Co. product was used as a detergent
  • distilled water filtered secondly as a filter of Mi 11 ipore Co. was used as distilled water.
  • ultrasonic washing was performed twice with distillation and water for 10 minutes.
  • isopropyl alcohol was ultrasonically washed with acetone and methane with a solvent, dried and then 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 following compound [HI ⁇ A] was thermally vacuum deposited to a thickness of 600 A on the prepared IT0 transparent electrode to form a hole injection layer.
  • 50 A and the following compound, [HT-A] (600 A) were sequentially vacuum deposited on the hole injection layer to form nuclei nitrile nucleated azatriphenylene (HAT), thereby forming a hole transport layer.
  • HAT nuclei nitrile nucleated azatriphenylene
  • Compound 1 prepared in Preparation Example 1 and the following compound [LiQKLithiumquinolate) were vacuum-deposited at a weight ratio of 1: 1 on the emission layer to form an electron injection and transport layer at a thickness of 350A.
  • Lithium fluoride (LiF) and 1.000 A thick aluminum were sequentially deposited on the electron injection and transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 A / sec, and the lithium fluoride at the cathode was 0.3 A / sec .
  • Aluminum maintained a deposition rate of .2 A / sec, and the vacuum degree during deposition was 1 X 10-7 to 5 10-8 torr.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using the compound shown in Table 1 below instead of compound 1 in Example 1-1.
  • Example 1-1 device was manufactured except that Compound (I) having the following structure was used instead of Compound 1 in Example 1-1.
  • Example 1-1 device was fabricated except that compound (II) having the following structure was used instead of compound 1 in Example 1-1.
  • Example 1-1 the organic light emitting device was manufactured in the same manner as in Example 1-1 except that instead of compound 1 to use the compound (III) in the structure.
  • the heterocyclic compound represented by Chemical Formula 1 when used in an organic material layer capable of simultaneously injecting electrons and transporting electrons, it is possible to mix and use n-type dopants used in the art. Accordingly, the heterocyclic compound represented by Formula 1 has a low driving voltage and high efficiency, and may improve stability of the device by hole stability of the compound.
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1.000A was placed in distilled water in which a detergent was dissolved and ultrasonically washed. At this time, Fischer Co. was used as a detergent. As distilled water, distilled water filtered secondly was used as a filter manufactured by Miller 11 (Mi 11 ipore Co.). After washing IT0 for 30 minutes, the ultrasonic washing was performed for 10 minutes by repeating the two distilled water. After the distilled water was washed, isopropyl alcohol was ultrasonically washed with a solvent of acetone and methanol, dried, and then transported to a plasma cleaner. In addition, the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • ITO indium tin oxide
  • Compound [HI-A] was vacuum-deposited to a thickness of 600 A on the ⁇ transparent electrode thus prepared to form a hole injection layer.
  • Nuclear nitrile nucleoaza E riphenylene (HAT) 50 A and compound [HT-A] (600A) were sequentially vacuum deposited on the hole injection layer to form a hole transport layer.
  • the light emitting layer was formed by vacuum deposition at a weight ratio of 25: 1.
  • Compound 1 prepared in Preparation Example 1 was vacuum-deposited on the emission layer to form an electron control layer with a thickness of 200 A.
  • the following compound [ET-1-J] and the compound [LiQKLithiimiquinolate) were vacuum-deposited in a 1: 1 increase ratio on the electron control layer to form an electron injection and transport layer at a thickness of 150A.
  • the electron injection and transport layer Lithium fluoride (Li F) and ⁇ , ⁇ thickness of 10A thickness were sequentially deposited on the cathode to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 A / sec.
  • the lithium fluoride of the negative electrode was 0.3 A / sec.
  • Aluminum maintained a deposition rate of 2 A / sec, and the vacuum degree during deposition was maintained at 1 X ⁇ 7 to 5 X 10 s torr. abandonment
  • Example 2-1 device was fabricated except that compound (I) having the above structure was used instead of compound 1 in Example 2-1.
  • Example 2-1 device was manufactured except that Compound (II) having the structure shown below was used instead of Compound 1 in Example 2-1.
  • An organic light emitting diode was manufactured according to the same method as Example 2-1 except for using Compound (III) having the following structure instead of Compound 1 in Example 2-1.
  • the heterocyclic compound represented by the formula (1) can be used in the electronic control insect of the organic light emitting device.
  • Example 2—1 to 2-23 is compared with Comparative Example 2-1.
  • Compounds substituted with only one side in the fluorene skeleton as in Chemical Formula 1 are excellent in thermal stability, and have a deep H0M0 level of 6. 0 eV or more.
  • Driving voltage in an organic light emitting device as compared to a compound having a high triplet energy (ET), and hole stability, symmetrically substituted on both sides in the fluorene skeleton. It can be seen that it shows excellent characteristics in terms of efficiency and lifespan.
  • ET triplet energy
  • Example 2—1 to 2-23 and Comparative Examples 2-2 and 2—3 are compared, Unlike compound (II) or (III) having anthracene as a substituent, compounds 1 to 23 in Examples 2-1 to 2-23 can be confirmed to have high color purity.
  • Substrate 2 Anode

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

Abstract

La présente invention concerne un nouveau composé et un dispositif électroluminescent organique le contenant, le nouveau composé comprenant un groupe fluorényle biphényle substitué ou non substitué en tant que structure noyau, l'un quelconque des cycles benzène dans le groupe fluorényle ayant deux groupes fonctionnels de structures différentes liés à celui-ci.
PCT/KR2018/002941 2017-04-12 2018-03-13 Nouveau composé et dispositif électroluminescent organique le contenant WO2018190522A1 (fr)

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US20190292169A1 (en) * 2018-03-23 2019-09-26 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US11563183B2 (en) 2017-06-21 2023-01-24 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US11588111B2 (en) 2017-08-04 2023-02-21 Samsung Display Co., Ltd. Condensed-cyclic compound and organic light-emitting device including the same

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WO2016141694A1 (fr) * 2015-03-09 2016-09-15 广东阿格蕾雅光电材料有限公司 Dispositif électroluminescent organique
WO2016141693A1 (fr) * 2015-03-09 2016-09-15 广东阿格蕾雅光电材料有限公司 Dispositif électroluminescent organique
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KR20160028524A (ko) * 2014-05-05 2016-03-11 메르크 파텐트 게엠베하 유기 발광 소자용 재료
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US11844273B2 (en) 2017-06-21 2023-12-12 Samsung Display Co., Ltd. Heterocyclic compound and organic light-emitting device including the same
US11588111B2 (en) 2017-08-04 2023-02-21 Samsung Display Co., Ltd. Condensed-cyclic compound and organic light-emitting device including the same
WO2019172649A1 (fr) * 2018-03-06 2019-09-12 주식회사 엘지화학 Composé polycyclique et élément électroluminescent organique le comprenant
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