WO2018208064A2 - Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant - Google Patents

Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant Download PDF

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WO2018208064A2
WO2018208064A2 PCT/KR2018/005278 KR2018005278W WO2018208064A2 WO 2018208064 A2 WO2018208064 A2 WO 2018208064A2 KR 2018005278 W KR2018005278 W KR 2018005278W WO 2018208064 A2 WO2018208064 A2 WO 2018208064A2
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group
formula
compound
light emitting
layer
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PCT/KR2018/005278
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WO2018208064A3 (fr
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허동욱
이동훈
허정오
장분재
한미연
양정훈
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주식회사 엘지화학
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Priority claimed from KR1020180051356A external-priority patent/KR102044429B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to CN201880004836.5A priority Critical patent/CN110036011B/zh
Publication of WO2018208064A2 publication Critical patent/WO2018208064A2/fr
Publication of WO2018208064A3 publication Critical patent/WO2018208064A3/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
    • C07D335/00—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom
    • C07D335/04—Heterocyclic compounds containing six-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D335/10—Dibenzothiopyrans; Hydrogenated dibenzothiopyrans
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/02—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings
    • C07D409/04—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing two hetero rings directly linked by a ring-member-to-ring-member bond
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D409/00—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms
    • C07D409/14—Heterocyclic compounds containing two or more hetero rings, at least one ring having sulfur atoms as the only ring hetero atoms containing three or more hetero rings
    • 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
    • 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 invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • organic light emitting phenomenon refers to a phenomenon of converting electrical energy into light energy using an organic material.
  • the organic light emitting device using the organic light emitting phenomenon has a wide viewing angle, excellent contrast, fast response time, excellent brightness, driving voltage and response speed characteristics, many studies have been conducted.
  • the organic light emitting device generally has a structure including an anode and a cathode and an organic material layer between the anode and the cathode.
  • the organic layer is often formed of a multilayer structure composed of different materials.
  • the organic material layer may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Patent Document 1 Korean Patent Publication No. 10— 2000-0051826
  • the present invention relates to a novel heterocyclic compound and an organic light emitting device comprising the same.
  • the present invention provides a compound represented by Formula 1:
  • Formula 2 E L is a direct bond; A substituted or unsubstituted C 6 - 60 arylene; Or a substituted or unsubstituted C 2 -60 heteroarylene including one or more heteroatoms selected from the group consisting of 0, N, Si, and S,
  • Xi to 5 are each independently N, or CH,
  • 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 includes a compound represented by Chemical Formula 1. .
  • the compound represented by Chemical Formula 1 may be used as a material of the organic material layer of the organic light emitting device, and may improve efficiency, low driving voltage, and / or lifespan characteristics in the value-added light emitting device.
  • the compound represented by Chemical Formula 1 may be used as a hole injection, hole transport, hole injection and transport, light emitting, electron transport, or electron injection material.
  • FIG. 1 shows an example of an organic light emitting element composed of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4. As shown in FIG.
  • FIG. 2 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a hole main pressure layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4 It is. 3 shows the 3D structure of the compounds of Formula 1-9. 4 shows a 3D structure of a compound of Formula 1-1, Formula ET-1-E. [Specific contents to carry out invention]
  • the 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.
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the ester group may be substituted with oxygen of the ester group having 1 to 25 carbon atoms, a branched or cyclic alkyl group or an aryl group having 6 to 25 carbon atoms.
  • it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited in this specification, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group is trimethylsilyl group, triethyl silyl group, t-butyldimethylsilyl group, vinyl dimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethyl boron group, t-butyldimethylboron group, triphenylboron group, phenylboron group, and the like.
  • examples of the halogen group include fluorine, chlorine, brim or iodine.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 40 carbon atoms. According to another 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.
  • alkyl group 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, nuclear chamber n n nuclear chamber, 1-methylpentyl, 2-methylpentyl, 4-methyl- 2-pentyl, 3, 3-dimethylbutyl, 2-ethylbutyl, Heptyl, n-heptyl, 1-methylnucleus, cyclopentylmethyl, cyclonuctylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylnuclear, 2-propylp
  • the alkenyl group may be linear or branched chain, Although carbon number is not specifically limited, It is preferable that it is 2-40. According to one embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • 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—phenyl vinyl— 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 groups, styrenyl groups, but not limited to these.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2, 3-dimethylcyclo.
  • the alkoxy group may be linear, branched or cyclic.
  • the carbon number of the alkoxy group is not particularly limited, but is preferably 1 to 60 carbon atoms.
  • the aryl group is not particularly limited, but preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one 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. no.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, peryllenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro group.
  • the heterocyclic group is a heterocyclic group containing one or more of 0, N, Si, and S as a dissimilar element, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • heterocyclic groups include thiophene group, furan group pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridil group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carbazole group, benzoxazole group, benzoimidazole group, benzothiazole group, benzocarbazole group, benzothiophene group, dibenzothiophene group, benzofuranyl group, phenanthroline
  • the heteroaryl 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 0, N, Se, S, and the like. Although carbon number is not particularly limited, it is preferably 2 to 60 carbon atoms, the heteroaryl group may be monocyclic or polycyclic.
  • heterocyclic groups include thiophene group, furanyl group, pyrrole group, imidazolyl group, thiazolyl group, oxazolyl group, oxadiazolyl group, pyridyl group, Bipyridyl, pyrimidyl, triazinyl, triazolyl, acridil, pyridazinyl, pyrazinyl, quinolinyl, quinazolinyl, quinoxalinyl, phthalazinyl and pyrido pyri Midyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinolinyl group, indolyl group, carbazolyl group, benzoxazolyl group, benzimidazolyl group, benzothiazolyl group, benzocarbazolyl group, benzo Thiophene group, dibenzothiophene group, benzofurany
  • the aryl group in the aralkyl group, the aralkenal group, the alkylaryl group, and the arylamine group is the same as the example of the aryl group described above.
  • the aralkyl group, the alkylaryl group, the alkylamine group and the vapor alkyl group are the same as the examples of the alkyl group described 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 description of the aryl group described above may be applied.
  • the description of the aforementioned heterocyclic group may be applied except that the heteroarylene is a divalent group.
  • the hydrocarbon ring is not a monovalent group, and the description of the aforementioned aryl group or cycloalkyl group may be applied except that two substituents are formed by bonding.
  • the hetero 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 arylene group refers to a divalent group having two bonding positions in the aryl group described above.
  • the description of the aforementioned aryl group can be applied except that they are each divalent.
  • the heteroarylene group is bonded to the heteroaryl group described above. Two positions means two. Except that they are each divalent, the above description of the heteroaryl group can be applied.
  • the present invention provides a compound represented by the formula (1).
  • S means a sulfur atom.
  • one of 3 ⁇ 4 to 3 ⁇ 4 is a functional group represented by Formula 2, and the rest may be hydrogen. That is, the compound may be represented by the following Formula 1-1, Formula 1-2, or Formula 1-3:
  • L and A are as defined above in the formula (1).
  • the compound of Formula 1 intervenes in conjugation in a non-covalent electron pair in a condensed ring of sulfur atoms, By providing abundant electrons in the condensed ring can exhibit an effect of strengthening the electron, hole mobility resulting from the heterocyclic group. Therefore, the organic light emitting device using the same may have high efficiency, low driving voltage, high brightness and long life.
  • the compound of Formula 1 serves as a sulfur atom for providing electrons. Because of the absence of the heterocyclic group, it may cause a problem of shortening the lifetime by inhibiting electron and hole mobility. More specifically, the dipole moment value of the compound in which the functional group represented by Chemical Formula 2 is bonded to one of 3 ⁇ 4 to 3 ⁇ 4 of Chemical Formula 1 is a substituent of the fluorene ring. About 10 times more than the dipole moment value of the compound bound to one of the can be confirmed, the conjugation effect by the sulfur atom described above.
  • L is a direct bond; A substituted or unsubstituted C 6 - 60 Ah tolylene; Or 1 heteroatom selected from the group consisting of 0 N, Si and S Substituted or unsubstituted C 2 -60 heteroarylene containing the above, more specific examples, L is a direct bond, or phenylene, or biphenylene, or naphthylene, or thiophenylene, or furanylene Or pyridinylene.
  • phenylene may be any one selected from the group consisting of:
  • Examples of the biphenylene may be selected from the group consisting of It can be one.
  • naphthylene may be one selected from the group consisting of:
  • Examples of the thiophenylene may be selected from the group consisting of It can be one.
  • Examples of the furanylene may be one selected from the group consisting of: Examples of the pyridinylene is one selected from the group consisting of
  • L may be any one selected from the group consisting of direct bonds or the following functional groups.
  • Arr & may be any one of the following Chemical Formulas 3 to 8,
  • 3 ⁇ 4 to ⁇ 5 are each independently ⁇ , or CH Yl to 3 ⁇ 4 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted d-60 alkyl; Substituted or unsubstituted C 3 -60 cycloalkyl; Substituted or unsubstituted HM aryl; Substituted or unsubstituted CHJO alkoxy; Substituted or unsubstituted C 2 -60 heteroaryl containing at least one heteroatom, each independently selected from the group consisting of N, 0, and S.
  • X to 5 are the same as or different from each other, each independently N, or CH, N is a nitrogen atom, in CH C is a carbon atom, H is a hydrogen atom bonded to a carbon atom Can be.
  • to Y 8 are the same or different from each other, and each independently hydrogen, phenyl biphenylyl, terphenylyl, dimethyl fluorenyl, naphthyl, phenylnaphthyl, pyridinyl, pyridinylphenyl , Dibenzofuranyl, dibenzothiophenyl, dibenzofuranylphenyl, dibenzothiophenylphenyl, trifluoromethoxy, or any one selected from the group consisting of:
  • A may be any one selected from the group consisting of the following functional groups.
  • the compound may be any one selected from the group consisting of the following compounds:
  • HOMO energy level of the compound represented by Formula 1 may be 6. 1 eV or more.
  • the HOMO energy level of the compound represented by Formula 1 is 6.0 eV or more, or 6.0 eV to its 0 eV, or 6.0 eV to 6.5 eV, or 6.0 eV to 6.4 eV, or 6.02 eV to 6.32 eV.
  • the energy level means the magnitude of energy. Therefore, even when the energy level is displayed in the negative ( ⁇ ) direction from the vacuum level, the energy level is interpreted to mean the absolute value of the corresponding energy value.
  • the H0M0 energy level is the highest occupied molecule from the vacuum level .
  • the distance to the orbital (highest occupi ed molecul ar orbi tal), the LUM0 energy level It means the distance from the low level to the lowest unoccupied molecular orbital.
  • the HOMO level may be measured using an atmospheric photoelectron spectroscopy apparatus (manufactured by RIKEN REIKI Co., Ltd .: AC3). Specifically, the HOMO level can be measured by irradiating 10 nW of UV at a 0.05 eV interval to the measurement sample deposited with a thickness of 100 nm, and measuring the amount of electrons accordingly.
  • an atmospheric photoelectron spectroscopy apparatus manufactured by RIKEN REIKI Co., Ltd .: AC3
  • the HOMO level can be measured by irradiating 10 nW of UV at a 0.05 eV interval to the measurement sample deposited with a thickness of 100 nm, and measuring the amount of electrons accordingly.
  • the present invention provides an organic light emitting device comprising the compound represented by the formula (1).
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light-emitting device including at least one organic material layer disposed between the first electrode and the second electrode, wherein at least one of the organic material layers includes 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.
  • the organic light emitting device of the present invention 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 light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic layer may include a hole injection layer, a hole transport layer, or a layer for simultaneously injecting and transporting holes, and the hole injection layer, a hole transport layer, or a layer for simultaneously injecting holes and transporting holes is represented by Formula 1 above. It may include a compound represented by.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1.
  • the electron transport layer, the electron injection layer, or may include a layer for performing both the electron transport and the electron injection, the electron transport layer, the electron injection layer, or the layer for simultaneously transporting and electron injection and the electron May contain a compound represented by 1.
  • the organic material layer may include a light emitting layer and an electron transport layer
  • the electron transport layer may include a compound represented by Chemical Formula 1.
  • the organic light emitting diode may include an electron blocking layer (EBL) positioned between the hole transport layer and the light emitting layer and / or a hole blocking layer positioned between the light emitting layer and the electron transport layer. layer: HBL) may be further included.
  • the compound represented by Formula 1 may be included in one or more layers of the electron blocking layer and the hole blocking layer.
  • the electron blocking layer and the hole blocking layer may be organic layers adjacent to each of the light emitting layers.
  • the compound represented by Formula 1 may be included in the light emitting layer, the electron transport layer or the hole blocking layer.
  • the organic material layer of the organic light emitting device of the present invention may consist of a single layer structure. However, it may be made of a multi-layered structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may include a hole injection layer and a hole transport layer between the first electrode and the light emitting layer, an electron transport layer and an electron injection layer between the light emitting layer and the second electrode, in addition to the light emitting layer as an organic layer.
  • the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
  • the organic light emitting diode according to the present invention 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 device may be an organic light emitting device 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 an organic light emitting device according to an embodiment of the present invention is illustrated in FIGS. 1 and 2.
  • FIG. 1 shows an example of an organic light emitting element consisting of a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • the compound represented by Formula 1 may be included in the light emitting layer.
  • the organic light emitting element consisting of a substrate 1, an anode 2, a hole injection layer 5, a hole transport layer 6, a light emitting layer 7, an electron transport layer 8 and a cathode 4; It is shown.
  • the compound represented by Formula 1 may be included in one or more layers of the hole injection layer, the hole transport layer, the light emitting layer and the electron transport layer.
  • the organic light emitting device according to the present invention may be manufactured by materials and methods known in the art, except that at least one of the organic material layers includes the compound represented by Chemical Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device may be manufactured by sequentially stacking a first electrode organic material layer and a second electrode on a substrate.
  • sputtering method Physical metal vapor deposition (PVD) methods, such as sputtering or e-beam evaporat ion, are used to deposit metal or conductive metal oxides or alloys thereof on a substrate.
  • PVD Physical metal vapor deposition
  • An anode may be formed, an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer may be formed thereon, and then, a material that may be used as a cathode may be deposited 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 represented by Chemical Formula 1 may be formed as an organic 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 coating, coating, etc., but is not limited to these.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material (W0 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode.
  • the anode material a material having a large work function is usually preferred to facilitate hole injection into the organic material layer.
  • the positive electrode material include barnapping, chromium, copper, zinc, and metals such as gold or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (IT0), zinc oxide (IZ0); ⁇ 0: ⁇ 1 or SN0 2 : A combination of a metal and an oxide such as Sb; Poly (3—methylthiophene) ⁇ poly [3,4- (ethylene-1,2-dioxy) thiophene] (PED0T), polypyrrole and polyaniline, such as but not limited to no. It is preferable that the cathode material is a material having a small work function to facilitate electron injection into the organic material layer.
  • the hole injection dance is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes.
  • the hole injection dance has an excellent hole injection effect for the light emitting layer or the light emitting material at the anode, and is produced in the light emitting layer. It is preferable to use a compound which prevents the migration of the filtered reporter to the electron injection layer or the electron injection material and is excellent in thin film formation ability.
  • HOMC highest occupied molecul ar orbital of the hole injection material is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injecting material include metal porphyr (in), oligothiophene, arylamine-based organic material, nucleonitrile nucleated azatriphenylene-based organic material, quinacridone-based organic material, and perylene ( perylene) 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 nonconjugated 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.
  • the light emitting layer may include a host material and a dopant material as described above.
  • the host material may further include a condensed aromatic ring derivative or a hetero ring-containing compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the hatero ring-containing compounds include carbazole derivatives and dibenzofuran. Derivatives, ladder type furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the dopant material is an aromatic amine derivative, a styrylamine compound, a boron complex, a fluoranthene compound ' , or a metal complex.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene and periplanthene having an aryl amino group, and substituted or unsubstituted styrylamine compounds.
  • aryl at least one compound of the aryl rings vinyl group value on the amine, an aryl group, a silyl group, an alkyl group, cycloalkyl group and aryl amino • a group of substituents selected more than one or two from the group consisting of is substituted or unsubstituted.
  • the metal complex includes an iridium complex and a platinum complex, but is not limited thereto.
  • the electron transport layer is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material that can be easily injected into the light emitting layer by injecting electrons from the cathode. Suitable. Specific examples 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, each followed by an aluminum layer or silver worm.
  • the electron injection layer is a charge for injecting electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from the cathode, has an excellent electron injection effect to the light emitting layer or the light emitting material, and holes of excitons generated in the light emitting layer
  • the compound which prevents the migration to an injection insect, and is excellent in thin film formation ability is preferable.
  • 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] qui Nolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc bis (2-methyl-8-quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (0— Cresolato) gallium, bis (2 -methyl-8-quinolinato) (1-naphlato) aluminum : bis (2-methyl-8-quinolinato) (2-naphlato) gallium, It is not limited to this.
  • the organic light emitting device 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 Formula 1 may be included in an organic solar cell or an organic transistor in addition to the organic light emitting device.
  • the above formula. Fabrication of the compound represented by 1 and the organic light emitting device including the same will be described in detail in the following Examples. However, the following examples are intended to illustrate the present invention, and the scope of the present invention is not limited thereto.
  • a compound represented by Chemical Formula E12 was prepared in the same manner as in Preparation Example 1, except that each starting material was used in the same manner as in the above Scheme.
  • a glass substrate coated with a thin film of I0 (indium t in oxide) of ⁇ , ⁇ was put in distilled water in which detergent was dissolved and ultrasonically washed.
  • Fischer Co. product was used as the detergent, and distilled water was filtered secondly as a filter of the Fiore Co. (Mi U ipore Co.) product.
  • ⁇ 0 was washed for 30 minutes, and then repeated twice with distilled water for 10 minutes. After washing with distilled water, ultrasonic washing with a solvent of isopropyl alcohol, acetone and methanol was carried out, dried and then transported to a plasma cleaner.
  • the substrate was washed 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 ⁇ 0 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 nuxaazatriphenylene (HAT) of the formula to form a hole transport layer.
  • HAT nuclei nitrile nuxaazatriphenylene
  • the compound of Formula [E1] and the following compound on the light emitting layer [LiQKLi thiumquinolate) was vacuum-deposited at a weight ratio of 1: 1 to form a? Transport layer with a thickness of 350A.
  • Lithium fluoride (LiF) and ⁇ , ⁇ thickness of 10A thickness were sequentially deposited on the electron transport layer to form an electron injection layer and a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 A / sec
  • the lithium fluoride at the cathode was maintained at 0.3 A / sec
  • the aluminum was maintained at 2 A / sec. by keeping the X 10- 7 to 5 X 10 _8 torr, it was produced in the organic light emitting device.
  • An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-A instead of the compound of Formula E1 in Example 1-1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Formula ET-1-B was used instead of the compound of Formula E1 in Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1 ′ C instead of the compound of Formula E1 in Example 1-1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Formula ET-1-D was used instead of the compound of Formula E1 in Example 1-1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Chemical Formula ET-1—E was used instead of the compound of Chemical Formula E1 in Example 1-1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Formula ET-1-F was used instead of the compound of Formula E1 in Example 1-1.
  • An organic light emitting diode was manufactured according to the same method as Example 1-1 except for using the compound of Formula ET-1-G instead of the compound of Formula E1 in Example 1-1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Formula ET-1-H was used instead of the compound of Formula E1 in Example 1-1.
  • An organic light-emitting device was manufactured in the same manner as in Example 1-1, except that the compound of Formula ET-1—I was used instead of the compound of Formula E1 in Example 1-1.
  • Example 1-1 instead of the compound of Formula E1, An organic light-emitting device was manufactured in the same manner as in Example 1-1, except for using a compound.
  • the organic light emitting diodes manufactured by the methods of Examples 1-1 to 1-18 and Comparative Examples 1-1 to 1-10 described above were measured for driving voltage and luminous efficiency at a current density of 10 mA / cm 2 .
  • the time (T 90 ) of 90% of the initial luminance at the current density of mA / cm 2 was measured. The results are shown in Table 1 below.
  • Example 1-9 according to an exemplary embodiment of the present specification 3 shows a 3D structure of a compound of Formula E9, it can be seen that the molecules of the compound has a horizontal structure, Comparative Example 1-5 According to FIG. 4, which shows the 3D structure of the ET— 1-E compound, the A and B axes are almost perpendicular to each other, indicating that the molecules deviate greatly from the horizontal structure.
  • the heterocyclic compound according to the exemplary embodiment of the present specification has a more horizontal structure according to the difference in the orientation (or i entat ion) on the 3D structure of the molecule. You can see the loss.
  • the compound in which only one heteroaryl group is substituted in the spiro fluorene thioxanthene skeleton has a horizontal structural tendency of the molecule as compared to a compound having two or more substituents. Due to the strong electron mobility, the driving voltage of the organic light emitting device is low, and high efficiency and long life are effective.
  • the structure of Formula 1 containing spiro fluorene thioxanthene is organic compared to the structure containing a spiro fluorene group It can be seen that the light emitting device exhibits excellent characteristics.
  • the HOMO energy is measured to be 6.02 eV to 6.32 eV, and as the energy level deepens, It was confirmed that the high mobility can exhibit excellent characteristics in terms of driving voltage, efficiency and lifetime when used in an organic light emitting device.
  • Substrate 2 tooth: the 0-ti Gutz
  • A direction of one axis
  • ⁇ direction of another axis

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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)
  • Plural Heterocyclic Compounds (AREA)

Abstract

La présente invention concerne un nouveau composé et un élément électroluminescent organique l'utilisant.
PCT/KR2018/005278 2017-05-12 2018-05-08 Nouveau composé hétérocyclique et élément électroluminescent organique l'utilisant WO2018208064A2 (fr)

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KR1020180051356A KR102044429B1 (ko) 2017-05-12 2018-05-03 신규한 헤테로 고리 화합물 및 이를 이용한 유기발광 소자

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