WO2020153652A1 - Composé, et élément électroluminescent organique le comprenant - Google Patents

Composé, et élément électroluminescent organique le comprenant Download PDF

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WO2020153652A1
WO2020153652A1 PCT/KR2020/000734 KR2020000734W WO2020153652A1 WO 2020153652 A1 WO2020153652 A1 WO 2020153652A1 KR 2020000734 W KR2020000734 W KR 2020000734W WO 2020153652 A1 WO2020153652 A1 WO 2020153652A1
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group
substituted
unsubstituted
light emitting
compound
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Korean (ko)
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서상덕
김민준
김동희
김서연
이다정
최승원
이동훈
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주식회사 엘지화학
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Priority to CN202080006295.7A priority Critical patent/CN113056463B/zh
Publication of WO2020153652A1 publication Critical patent/WO2020153652A1/fr

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    • 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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D405/00—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom
    • C07D405/14—Heterocyclic compounds containing both one or more hetero rings having oxygen atoms as the only ring hetero atoms, and one or more rings having nitrogen as the only ring hetero atom containing three or more hetero rings
    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D491/00—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00
    • C07D491/02—Heterocyclic compounds containing in the condensed ring system both one or more rings having oxygen atoms as the only ring hetero atoms and one or more rings having nitrogen atoms as the only ring hetero atoms, not provided for by groups C07D451/00 - C07D459/00, C07D463/00, C07D477/00 or C07D489/00 in which the condensed system contains two hetero rings
    • C07D491/04—Ortho-condensed systems
    • C07D491/044—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring
    • C07D491/048—Ortho-condensed systems with only one oxygen atom as ring hetero atom in the oxygen-containing ring the oxygen-containing ring being five-membered
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
    • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
    • C07D495/04—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
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting device is a light emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between the electrode and the organic semiconductor material.
  • the organic light emitting device can be roughly divided into two types according to the operation principle. First, excitons are formed in the organic layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting device of the form.
  • the second is a light emitting device in which holes and/or electrons are injected into a layer of an organic semiconductor material that interfaces with an electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • the organic light emitting phenomenon refers to a phenomenon that converts 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 and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layer structure composed of different materials, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, an electron injection layer, etc. Can lose.
  • Materials used as an organic material layer in the organic light emitting device may be classified into light emitting materials and charge transport materials, such as hole injection materials, hole transport materials, electron suppressing materials, electron transport materials, and electron injection materials, depending on their function.
  • the light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.
  • a host/dopant system may be used as a light emitting material in order to increase color purity and increase light emission efficiency through energy transfer.
  • the principle is that when a small amount of a dopant having a smaller energy band gap and a higher luminous efficiency is mixed with a light emitting layer than a host mainly constituting the light emitting layer, excitons generated from the host are transported as a dopant to produce high efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used.
  • materials constituting an organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron suppressing material, an electron transport material, an electron injection material, are stable and efficient materials It is supported by, and the development of new materials continues to be required.
  • One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.
  • X is O or S
  • Ar is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a and B is substituted or unsubstituted benzene, and the other is substituted or unsubstituted naphthalene,
  • R1 and R2 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Or a substituted or unsubstituted alkyl group,
  • r1 is an integer from 0 to 4,
  • r2 is an integer from 0 to 2
  • Another exemplary embodiment is a first electrode; A second electrode provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, and at least one layer of the organic material layer provides an organic light emitting device including the above-described compound.
  • the compound represented by Chemical Formula 1 of the present invention can be used as a material for the organic material layer of the organic light emitting device.
  • the organic light emitting diode including the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification can improve the efficiency.
  • the organic light emitting diode including the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification can improve the lifespan characteristics.
  • FIG. 1 shows an organic light emitting diode according to an exemplary embodiment of the present specification.
  • FIG. 2 illustrates an organic light emitting diode according to another exemplary embodiment of the present specification.
  • FIG 3 illustrates an organic light emitting device according to another exemplary embodiment of the present specification.
  • the organic light emitting diode including the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification can improve the efficiency.
  • the organic light emitting diode including the compound represented by Chemical Formula 1 according to an exemplary embodiment of the present specification can improve the lifespan characteristics.
  • the compound represented by Formula 1 herein is composed of a quinoxaline unit serving as an electron acceptor and a carbazole unit condensed with a ring serving as an electron donor. Because these two units are directly coupled, the band gap is reduced by exchanging charges inside and outside the molecule.
  • the naphthalene ring is located in one of A or B of Formula 1 of the present application, the triplet energy is lowered. As a result, both the singlet energy and the triplet energy are small, which is advantageous for energy transfer to the red dopant, so as a host of the red light emitting layer It is appropriate to use.
  • oxygen or sulfur atoms are located at the meta position based on the nitrogen of the carbazole, and the ring is condensed.
  • the ortho position does not push electrons well with nitrogen electrons, and the para position is The meta position acts as an appropriate electron donor, while pushing too hard. At the same time, it has a more stable structure than carbazole units with substituents due to condensed rings.
  • the carbazole unit in which the Ar unit and the ring are condensed are substituted at the ortho position, so that they face each other due to structural interference between the two. It shows the characteristics of long life.
  • substitution means that the hydrogen atom bonded to the 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 the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
  • substituted or unsubstituted in this specification is deuterium (-D); Halogen group; Nitrile group; Nitro group; Hydroxy group; Silyl group; Boron group; Alkoxy groups; Alkyl groups; Cycloalkyl group; Aryl group; And one or two or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents of the above-exemplified substituents, or having no substituents.
  • a substituent having two or more substituents 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 connected.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
  • the silyl group may be represented by the formula of -SiYaYbYc, wherein Ya, Yb and Yc are each hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; It may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
  • the silyl group specifically includes, but is not limited to, trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like. Does not.
  • the boron group may be represented by the formula of -BYdYe, wherein Yd and Ye are each hydrogen; heavy hydrogen; halogen; Nitrile group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; It may be a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group.
  • the boron group may include, but is not limited to, trimethyl boron group, triethyl boron group, tert-butyl dimethyl boron group, triphenyl boron group, phenyl boron group, and the like.
  • the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 30 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 group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but is not limited to these.
  • the alkenyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30.
  • 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, steelbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms.
  • Substituents comprising alkyl, alkoxy, and other alkyl group moieties described herein include both straight-chain or ground forms.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary 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, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 20. According to one embodiment, the carbon number of the aryl group is 6 to 30.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.
  • the fluorene group may be substituted, and two substituents may combine with each other to form a spiro structure.
  • Spirofluorene groups such as (9,9-dimethylfluorene group
  • It may be a substituted fluorene group such as (9,9-diphenylfluorene group).
  • substituted fluorene group such as (9,9-diphenylfluorene group
  • the heterocyclic group is a hetero atom and is a ring group containing one or more of N, O, P, S, Si, and Se, and carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the heterocyclic group has 2 to 20 carbon atoms.
  • heterocyclic group examples include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazine group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, Carbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, indenocarbazole group, indolocarbazole group, and the like, but are not limited thereto.
  • heterocyclic group may be applied, except that the heteroaryl group is aromatic.
  • X is O or S.
  • Ar is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • Ar is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • Ar is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • Ar is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted bicyclic heterocyclic group containing N, O or S.
  • Ar is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; A substituted or unsubstituted benzoxazole group; Or a substituted or unsubstituted benzothiazole group.
  • Ar is a phenyl group unsubstituted or substituted with an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; A biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A carbazole group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; A dibenzofuran group unsubstituted or substituted with an alkyl group or an aryl group; A dibenzothiophene group unsubstituted or substituted with an alkyl group or an aryl group; A benzoxazole group unsubstituted or substituted with an alkyl group
  • Ar is a phenyl group; Naphthyl group; Biphenyl group; Terphenyl group; A carbazole group unsubstituted or substituted with a phenyl group; A fluorene group unsubstituted or substituted with a methyl group; Dibenzofuran group; Dibenzothiophene group; Or a benzothiazole group.
  • Ar is a phenyl group; Naphthyl group; Biphenyl group; Terphenyl group; A carbazole group unsubstituted or substituted with a phenyl group; Dimethylfluorene group; Dibenzofuran group; Dibenzothiophene group; Or a benzothiazole group.
  • Ar is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted dibenzofuran group; Or a substituted or unsubstituted dibenzothiophene group.
  • Ar is a phenyl group; Naphthyl group; Biphenyl group; Dimethylfluorene group; A carbazole group unsubstituted or substituted with a phenyl group; Dibenzofuran group; Or dibenzothiophene group.
  • Ar may be represented by any one of the following structures.
  • B1 to B13 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • b1 is an integer from 0 to 5
  • b2 is an integer from 0 to 9
  • b3 is an integer from 0 to 13
  • b4 to b7 are each an integer from 0 to 7,
  • b8 is an integer from 0 to 8
  • b9 is an integer from 0 to 4,
  • b10 is an integer from 0 to 7
  • Ar may be represented by any one of the following structures.
  • the dotted line means the bonding position.
  • Ar may be represented by any one of the following structures.
  • the dotted line means the bonding position.
  • B1 to B10 is hydrogen.
  • B11 to B13 are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • B11 to B13 are each independently substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • B11 to B13 are each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • B11 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
  • B11 is a substituted or unsubstituted phenyl group.
  • B11 is a phenyl group.
  • B12 and B13 are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
  • B12 and B13 is a methyl group.
  • b1 to b10 is 0 or 1.
  • b1 to b10 is 0.
  • one of A and B is substituted or unsubstituted benzene, and the other is substituted or unsubstituted naphthalene.
  • one of A and B is benzene, the other is naphthalene.
  • Chemical Formula 1 may be represented by any one of the following Chemical Formulas 2 to 7.
  • Ar, X, R1, R2, r1 and r2 are the same as defined in Formula 1,
  • A1 and A2 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Or a substituted or unsubstituted alkyl group,
  • a1 is an integer from 0 to 6
  • a2 is an integer from 0 to 4,
  • R1, R2, A1 and A2 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Or a substituted or unsubstituted alkyl group.
  • R1, R2, A1 and A2 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Or a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R1, R2, A1 and A2 are each independently hydrogen; heavy hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
  • R1, R2, A1 and A2 are each independently hydrogen; Or a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
  • R1 is hydrogen
  • R2 is hydrogen
  • A1 is hydrogen
  • A2 is hydrogen
  • r1 is an integer of 0 to 4.
  • r1 is an integer of 0 to 1.
  • r2 is an integer of 0 to 2.
  • r2 is an integer of 0 to 1.
  • r1 and r2 are 2 or more, structures in two or more parentheses are the same or different from each other.
  • R1 when r1 is 2 or more, two or more R1 are the same as or different from each other.
  • the two R2 are the same or different from each other.
  • a1 is an integer of 0 to 6.
  • a1 is an integer of 0 to 1.
  • a2 is an integer of 0 to 4.
  • a2 is an integer of 0 to 1.
  • the formula 1 may be represented by any one of the following compounds.
  • the compound represented by Formula 1 of the present specification may have a core structure as shown in the following reaction formula.
  • Substituents can be combined by methods known in the art, and the type, location, and number of substituents can be varied according to techniques known in the art.
  • X and Ar are as defined in Formula 1, and Z are each independently a halogen group.
  • compounds having various energy band gaps may be synthesized by introducing various substituents to the core structure as described above.
  • the HOMO and LUMO energy levels of the compound can be adjusted by introducing various substituents to the core structure having the above structure.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least one layer of an organic material provided between the first electrode and the second electrode, and at least one layer of the organic material layer comprises the above-described compound.
  • the organic light-emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light-emitting device, except that one or more organic material layers are formed using the compound represented by Chemical Formula 1 above.
  • an organic light emitting device having an organic material layer including the compound represented by Compound 1 it may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method.
  • the solution application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • the organic material layer of the organic light emitting device of the present specification may have a single layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention is a hole transport layer, a hole injection layer, an electron blocking layer, a layer simultaneously performing hole transport and hole injection, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection simultaneously as an organic material layer. It may have a structure including one or more of the layers.
  • the structure of the organic light emitting device of the present specification is not limited thereto, and may include fewer or more organic material layers.
  • the organic material layer includes a hole transport layer or a hole injection layer, and the hole transport layer or the hole injection layer may include a compound represented by Formula 1 described above.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or the electron injection layer may include a compound represented by Formula 1 described above.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 described above.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include the compound as a host of the light emitting layer.
  • the emission layer includes the compound represented by Chemical Formula 1 as a host of the emission layer, and may further include a dopant.
  • the content of the dopant may be included in 1 part by weight to 60 parts by weight based on 100 parts by weight of the host, preferably 1 part by weight to 20 parts by weight, and more preferably 1 part by weight to 10 parts by weight .
  • the dopant is (4,6-F2ppy) 2 phosphor, such as Irpic, spiro-DPVBi, spiro-6P, distylbenzene (DSB), distriarylene (DSA), PFO-based polymer, PPV-based Fluorescent materials such as polymers, anthracene-based compounds, pyrene-based compounds, and boron-based compounds may be used, but are 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 organic light emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 to 3, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer 3.
  • an anode 2 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 are sequentially stacked on an organic light emitting device on a substrate 1
  • the structure is illustrated. In such a structure, the compound may be included in the light emitting layer 7.
  • an anode 2 a hole injection layer 5, a hole transport layer 6, an electron blocking layer 9, a light emitting layer 7, an electron transport and injection layer 10, and a cathode 4 on the substrate 1 ) Is a structure of an organic light-emitting device sequentially stacked. In such a structure, the compound may be included in the light emitting layer 7.
  • the organic light emitting device uses a metal vapor deposition (PVD) method, such as sputtering or e-beam evaporation, to have a metal or conductive metal oxide on the substrate or alloys thereof
  • PVD metal vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer, and an electron injection layer, and then depositing a material that can be used as a cathode thereon Can be.
  • an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the organic material layer may be a multi-layer structure including a hole injection layer, a hole transport layer, an electron injection and electron transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron injection and electron transport layer, and the like.
  • the present invention is not limited thereto, and may be a single-layer structure.
  • the organic material layer has a smaller number of solvent processes, such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than deposition using various polymer materials. Can be prepared in layers.
  • the positive electrode is an electrode for injecting holes
  • a positive electrode material is preferably a material having a large work function to facilitate hole injection into an organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole and polyaniline, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into an 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;
  • There is a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer that serves to smoothly inject holes from the anode to the light emitting layer.
  • a hole injection material can be well injected with holes from the anode, and HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
  • the hole injection layer may have a thickness of 1 to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from being deteriorated, and when it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement. There is an advantage that can be prevented.
  • the hole transport layer may serve to facilitate the transport of holes.
  • a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer is suitable for a material having high mobility for holes.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron blocking layer may be a material known in the art.
  • the light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • a material capable of emitting light in the visible region by receiving and bonding holes and electrons from the hole transport layer and the electron transport layer, respectively is preferably a material having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq3); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzo quinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole compounds; Poly(p-phenylenevinylene) (PPV) polymers; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited to these.
  • Alq3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzo quinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole compounds Benzoxazole, benzthiazole and benzimidazole compounds
  • Poly(p-phenylenevinylene) (PPV) polymers Spiro compounds
  • Polyfluorene, rubrene, and the like but are not limited to these.
  • the light emitting layer may include a compound represented by Formula 1 herein, and specifically, a compound represented by Formula 1 herein may be included as a host. Specifically, when the compound represented by Formula 1 herein is used as a host for a light emitting layer, it may be used as a phosphorescent material emitting red light.
  • PIQIr(acac)(bis(1-phenylisoquinoline)acetylacetonateiridium), PQIr(acac)(bis(1-phenylquinoline)acetylacetonate iridium), PQIr(tris(1-phenylquinoline)iridium are used as the light emitting dopant.
  • a phosphorescent material such as PtOEP (octaethylporphyrin platinum), or a fluorescent material such as Alq3 (tris(8-hydroxyquinolino)aluminum) may be used, but is not limited thereto.
  • the emission layer may further include a compound represented by the following Chemical Formula 8.
  • the light emitting layer may include a compound represented by Formula 8 as an additional host.
  • the compound represented by Chemical Formula 1 based on 100 parts by weight of the whole host may be included in 10 to 70 parts by weight, and preferably 20 to 50 parts by weight.
  • R a and R b are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • R c and R d are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Amino group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms containing any one or more selected from the group consisting of N, O and S,
  • r and s are each an integer of 0 to 7, and when r is 2 or more, R c is the same or different from each other, and when s is 2 or more, Rd is the same or different from each other.
  • R c and R d are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Amino group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted alkenyl group having 2 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms containing any one or more selected from the group consisting of N, O and S.
  • R c and R d is hydrogen.
  • R a and R b are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • R a and R b are the same as or different from each other, and each independently substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R a and R b are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted carbazole group; A substituted or unsubstituted fluorene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted benzothiazole group.
  • R a and R b are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with an alkyl group or an aryl group; A biphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A terphenyl group unsubstituted or substituted with an alkyl group or an aryl group; A naphthyl group unsubstituted or substituted with an alkyl group or an aryl group; A fluorene group unsubstituted or substituted with an alkyl group or an aryl group; A dibenzofuran group unsubstituted or substituted with an alkyl group or an aryl group; Or a dibenzothiophene group unsubstituted or substituted with an alkyl group or an aryl group.
  • R a and R b are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group; A biphenyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group; A terphenyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group; A naphthyl group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group; A fluorene group unsubstituted or substituted with a methyl group, a phenyl group, or a naphthyl group; A dibenzofuran group unsubstituted or substituted with a methyl group, a phenyl group,
  • R a and R b are the same as or different from each other, and each independently a phenyl group unsubstituted or substituted with a phenyl group or a naphthyl group; Biphenyl group; Terphenyl group; A naphthyl group unsubstituted or substituted with a phenyl group; Dimethylfluorene group; Dibenzofuran group; Or dibenzothiophene group.
  • R a and R b may be represented by any one of the following structures, respectively.
  • C1 to C13 are each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group,
  • c1 is an integer from 0 to 5
  • c2 is an integer from 0 to 9
  • c3 is an integer from 0 to 13
  • c4 to c7 are each an integer from 0 to 7,
  • c8 is an integer from 0 to 8
  • c9 is an integer from 0 to 4,
  • c10 is an integer from 0 to 7
  • C1 to C10 is hydrogen.
  • C11 to C13 are each independently a substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • C11 to C13 are each independently substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • C11 to C13 are each independently substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • C11 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
  • C11 is a substituted or unsubstituted phenyl group.
  • C11 is a phenyl group.
  • C12 and C13 are each independently a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms.
  • C12 and C13 is a methyl group.
  • R a and R b may be represented by any one of the following structures, respectively.
  • C1 to C3, C5 to C7, C10, C12, C13, c1 to c3, c5 to c7 and c10 are as described above.
  • r and s are each an integer of 0 to 7.
  • r and s is 0 or 1, respectively.
  • Formula 8 may be represented by any one of the following compounds.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transport material a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include the Al complex of 8-hydroxyquinoline; Complexes including Alq3; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the thickness of the electron transport layer may be 1 to 50 nm. If the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing the electron transport properties from deteriorating, and if it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from rising to improve the movement of electrons. There is an advantage.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect on the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , A compound having excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-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)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the electron blocking layer is a layer that prevents the cathode from reaching 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 complex, and the like, but are not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
  • ITO Indium Tin Oxide
  • distilled water filtered secondarily by a filter of Millipore Co.
  • ultrasonic washing was repeated 10 times with distilled water for 10 minutes.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying and transporting to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • HI-A and hexanitrile hexaazatriphenylene (HAT-CN) on the ITO transparent electrode thus prepared were sequentially thermal vacuum deposited to a thickness of 800 Pa and 50 Pa, respectively, to form a hole injection layer.
  • the following HT-A as a hole transport layer was vacuum-deposited to a thickness of 800 MPa, and then EB-A as an electron blocking layer was thermally vacuum-deposited to a thickness of 600 MPa.
  • the host RH-A and the dopant RD of 2 wt% based on 100 parts by weight of the host were vacuum-deposited to a thickness of 400 Pa as a light emitting layer.
  • the following ET-A and Liq as an electron transport and injection layer were thermally vacuum-deposited to a thickness of 360 MPa at a ratio of 1:1, and then Liq was vacuum-deposited to a thickness of 5 MPa.
  • magnesium and silver were sequentially deposited at a thickness of 220 ⁇ at a ratio of 10:1, and aluminum was formed at a thickness of 1000 ⁇ to form a cathode, thereby manufacturing an organic light emitting device.
  • Comparative Example 1-1 instead of RH-A, as shown in Table 1, using the same method as in Comparative Example 1-1, Examples 1-1 to 1-22 and Comparative Examples The organic light-emitting devices of 1-2 to Comparative Examples 1-7 were produced, respectively.
  • the compound represented by Formula 1 of the present invention is composed of a quinoxaline unit serving as an electron acceptor and a carbazole unit condensed with a ring serving as an electron donor. Because these two units are directly coupled, the band gap is reduced by exchanging charges inside and outside the molecule. In addition, since the naphthalene ring is located in one of A or B, the triplet energy is lowered. As a result, the singlet energy and triplet energy are both small, which is advantageous for energy transfer to the red dopant, and as shown in Table 1, the host of the red light emitting layer It is suitable to use as.
  • the band gap is too large, or if the triplet energy is too small due to the position of naphthalene units in positions A and B of Formula 1 like RH-F, the red dopant As the energy transfer to the furnace is not smooth, voltage, efficiency, and lifetime are all poor.
  • the ring is condensed due to the oxygen or sulfur atom located at the meta position based on the nitrogen of the carbazole, and the hetero atom is in the para position, such as RH-E, or RH-D
  • the nitrogen atom comes, the electron donating property becomes too strong, and the HOMO (Highest Occupied Molecular Orbital) energy level is too high, so the hole injection is not smooth and the voltage rises.
  • Formula 1 of the present invention based on the quinoxaline unit, Ar units and carbazole units condensed with rings are substituted at ortho positions to each other, and thus have mutually opposite characteristics. Due to the action, the structure is more stabilized, showing the characteristics of long life. This can be seen through comparison with the RH-C structure using a quinazoline unit as an electron acceptor structure instead of a quinoxaline unit.
  • the band gap is larger than the compound of the formula 1 of the present invention in which the electron donor unit and the electron carbazole derivative are directly bonded. Therefore, energy transfer to the dopant is not smooth, reducing efficiency and life.
  • Comparative Example 1-1 except for using a mixture of two host compounds as shown in Table 2 instead of RH-A, using the same method as Comparative Example 1-1, Examples 2-1 to The organic light emitting devices of Examples 2-14 and Comparative Examples 2-1 to Comparative Examples 2-3 were manufactured, respectively. In this case, when a mixture of two types of compounds is used as the host, the parentheses indicate the weight ratio between the host compounds.
  • Example 2-1 PGH1: Compound 1 (70:30) 4.63 21.4 121
  • Example 2-2 PGH1: Compound 5 (70:30) 4.67 21.8 127
  • Example 2-3 PGH1: Compound 6 (70:30) 4.85 20.0 90
  • Example 2-4 PGH1: Compound 8 (70:30) 4.76 21.5 106
  • Example 2-5 PGH1: Compound 10 (70:30) 4.77 21.1 101
  • Example 2-10 PGH1: Compound 20 (70:30) 4.61 21.6 104
  • Example 2-10 PGH1: Compound 20

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Abstract

La présente invention concerne : un composé représenté par la formule chimique 1; et un élément électroluminescent organique le comprenant.
PCT/KR2020/000734 2019-01-25 2020-01-15 Composé, et élément électroluminescent organique le comprenant WO2020153652A1 (fr)

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