WO2019143224A1 - Composé polycyclique et diode électroluminescente organique le comprenant - Google Patents

Composé polycyclique et diode électroluminescente organique le comprenant Download PDF

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WO2019143224A1
WO2019143224A1 PCT/KR2019/000903 KR2019000903W WO2019143224A1 WO 2019143224 A1 WO2019143224 A1 WO 2019143224A1 KR 2019000903 W KR2019000903 W KR 2019000903W WO 2019143224 A1 WO2019143224 A1 WO 2019143224A1
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group
substituted
compound
layer
light emitting
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Korean (ko)
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정민우
이동훈
장분재
이정하
한수진
박슬찬
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주식회사 엘지화학
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Priority to CN201980003801.4A priority Critical patent/CN111032649B/zh
Publication of WO2019143224A1 publication Critical patent/WO2019143224A1/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
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D251/00—Heterocyclic compounds containing 1,3,5-triazine rings
    • C07D251/02—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings
    • C07D251/12—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members
    • C07D251/14—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom
    • C07D251/24—Heterocyclic compounds containing 1,3,5-triazine rings not condensed with other rings having three double bonds between ring members or between ring members and non-ring members with hydrogen or carbon atoms directly attached to at least one ring carbon atom to three ring carbon atoms
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing three or more hetero rings
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    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • 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
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
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    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1059—Heterocyclic compounds characterised by ligands containing three nitrogen atoms as heteroatoms
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    • 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
    • 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]
    • H10K50/14—Carrier transporting layers
    • H10K50/16—Electron transporting layers
    • 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

Definitions

  • the present invention relates to a polycyclic compound and an organic light emitting device comprising the same.
  • an organic light emitting element is a light emitting element using an organic semiconductor material, and requires the exchange of holes and / or electrons between the electrode and the organic semiconductor material.
  • the organic light emitting device can be roughly classified into two types according to the operating principle as described below. First, an exciton is formed in an organic material layer by a photon introduced into an element from an external light source. The exciton is separated into an electron and a hole, and the electrons and holes are transferred to different electrodes to be used as a current source Emitting device.
  • the second type is a light emitting device that injects holes and / or electrons into an organic semiconductor material layer that interfaces with the electrode by applying a voltage or current to two or more electrodes, and operates by injected electrons and holes.
  • organic light emission phenomenon refers to a phenomenon in which an organic material is used to convert electric energy into light energy.
  • An organic light emitting device using an organic light emitting phenomenon generally has a structure including an anode, a cathode, and an organic material layer therebetween.
  • the organic material layer may have a multi-layer structure composed of different materials and may include a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, and an electron injection layer.
  • Such an organic light emitting device When a voltage is applied between the two electrodes in the structure of such an organic light emitting device, holes are injected in the anode, electrons are injected into the organic layer in the cathode, excitons are formed when injected holes and electrons meet, When it falls back to the ground state, the light comes out.
  • Such an organic light emitting device is known to have characteristics such as self-emission, high luminance, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • a material used as an organic material layer in an organic light emitting device can be classified into a light emitting material and a charge transporting material such as a hole injecting material, a hole transporting material, an electron transporting material, and an electron injecting material depending on functions.
  • the luminescent material has blue, green and red luminescent materials and yellow and orange luminescent materials necessary for realizing a better natural color depending on the luminescent color.
  • a host / dopant system can be used as a light emitting material.
  • the principle is that when a small amount of dopant having a smaller energy band gap and higher luminous efficiency than a host mainly constituting the light emitting layer is mixed with a light emitting layer in a small amount, the excitons generated in the host are transported as a dopant to emit light with high efficiency. At this time, since the wavelength of the host is shifted to the wavelength band of the dopant, light of a desired wavelength can be obtained depending on the type of the dopant used.
  • materials constituting the organic material layer in the device such as a hole injecting material, a hole transporting material, a light emitting material, an electron transporting material and an electron injecting material are supported by stable and efficient materials Development of new materials is continuously required.
  • X1 to X6 and Y1 to Y6 each independently represent N or CR
  • At least two of X1 to X3, at least two of X4 to X6, at least two of Y1 to Y3 and at least two of Y4 to Y6 are N,
  • R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,
  • R1 is a substituted or unsubstituted aryl group
  • R2 and R3 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a is an integer of 0 to 7
  • b is an integer of 1 to 8
  • R &lt when L2 is a direct bond, R < 3 > is deuterium; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent R3's are bonded to each other to form a ring.
  • a plasma display panel comprising: a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.
  • the compound described in this specification can be used as a material of an organic layer of an organic light emitting device.
  • the compound according to at least one embodiment can improve the life characteristics in the organic light emitting device and / or the organic light emitting device.
  • the compounds described in this specification can be used as materials for the hole injecting layer, the hole transporting layer, the electron blocking layer, the light emitting layer, the hole blocking layer, the electron transporting layer and the electron injecting layer.
  • Fig. 1 shows an example of an organic light-emitting device comprising a substrate 1, an anode 2, a light-emitting layer 3 and a cathode 4.
  • FIG. 2 shows an example of an organic light emitting element comprising a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 It is.
  • the present invention provides a compound represented by the following formula (1) or (2).
  • the compound represented by the formula (1) or (2) is used for the organic material layer of the organic light emitting device, the efficiency of the organic light emitting device is always maintained.
  • X1 to X6 and Y1 to Y6 each independently represent N or CR
  • At least two of X1 to X3, at least two of X4 to X6, at least two of Y1 to Y3 and at least two of Y4 to Y6 are N,
  • R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • L1 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heterocyclic group,
  • R1 is a substituted or unsubstituted aryl group
  • R2 and R3 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a is an integer of 0 to 7
  • b is an integer of 1 to 8
  • R &lt when L2 is a direct bond, R < 3 > is deuterium; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or adjacent R3's are bonded to each other to form a ring.
  • a member when a member is located on another member, it includes not only the case where the member is in contact with the other member but also the case where another member exists between the two members.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • substituted or unsubstituted A halogen group; Cyano; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted arylamine group; A substituted or unsubstituted aryl group; And a substituted or unsubstituted heterocyclic group, or that at least two of the substituents exemplified above are substituted with a substituent to which they are linked, or have no substituent.
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent in which two phenyl groups are connected.
  • examples of the halogen group include fluorine (F), chlorine (Cl), bromine (Br) or iodine (I).
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another embodiment, the alkyl group has 1 to 20 carbon atoms. According to another embodiment, the alkyl group has 1 to 10 carbon atoms. Specific examples of the alkyl group include a methyl group, an ethyl group, an n-propyl group, an isopropyl group, a n-butyl group, an isobutyl group, a tert- And a til group, but are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms. According to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specific examples thereof include, but are not limited to, a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, and a cyclooctyl group.
  • examples of the arylamine group include a substituted or unsubstituted monoarylamine group, a substituted or unsubstituted diarylamine group, or a substituted or unsubstituted triarylamine group.
  • the aryl group in the arylamine group may be a monocyclic aryl group or a polycyclic aryl group.
  • the arylamine group containing two or more aryl groups may contain a monocyclic aryl group, a polycyclic aryl group, or a monocyclic aryl group and a polycyclic aryl group at the same time.
  • arylamine group examples include a phenylamine group, a naphthylamine group, a biphenylamine group, an anthracenylamine group, a 3-methylphenylamine group, a 4-methylnaphthylamine group, Group, a 9-methyl-anthracenylamine group, a diphenylamine group, a phenylnaphthylamine group, a biphenylphenylamine group, and the like, but the present invention is not limited thereto.
  • 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 one embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group or the like as the monocyclic aryl group, but is not limited thereto.
  • polycyclic aryl group examples include, but are not limited to, a naphthyl group, an anthracenyl group, a phenanthrenyl group, a pyrenyl group, a perylenyl group, a triphenyl group, a klycenyl group and a fluorenyl group.
  • a fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the present invention is not limited thereto.
  • the heterocyclic group is a heteroaromatic ring group containing at least one of N, O, P, S, Si and Se.
  • the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to one embodiment, the number of carbon atoms of the heterocyclic group is 2 to 30.
  • the heterocyclic group include a pyridyl group, a pyrrolyl group, a pyrimidyl group, a pyridazinyl group, a furanyl group, a thiophenyl group, an imidazole group, a pyrazole group, a dibenzofuranyl group and a dibenzothiophenyl group.
  • the present invention is not limited thereto.
  • heterocyclic group in the present specification, the description of the aforementioned heterocyclic group can be applied, except that the heteroaryl group is aromatic.
  • adjacent The group may mean a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom of the substituent.
  • two substituents substituted at the ortho position in the benzene ring and two substituents substituted at the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • the "ring” means a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.
  • the hetero ring includes one or more non-carbon atoms and hetero atoms.
  • the hetero atom includes at least one atom selected from the group consisting of N, O, P, S, Si and Se can do.
  • the heterocyclic ring may be monocyclic or polycyclic, and may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and the aromatic heterocyclic ring may be selected from the examples of the heteroaryl group except that it is not monovalent.
  • the formula (1) is represented by any one of the following formulas (3) to (6).
  • X1 to X3, Y1 to Y3, L1, R1, R2 and a are as defined above.
  • X1 and X2 are N and X3 is CR.
  • X1 and X3 are N and X2 is CR.
  • X2 and X3 are N and X1 is CR.
  • X1 to X3 are N.
  • Y1 and Y2 are N and Y3 is CR.
  • Y1 and Y3 are N and Y2 is CR.
  • Y2 and Y3 are N and Y1 is CR.
  • Y1 to Y3 are N.
  • X4 and X5 are N and X6 is CR.
  • X4 and X6 are N and X5 is CR.
  • X5 and X6 are N and X4 is CR.
  • X4 to X6 are N.
  • Y4 and Y5 are N and Y6 is CR.
  • Y4 and Y6 are N and Y5 is CR.
  • Y5 and Y6 are N and Y4 is CR.
  • Y4 to Y6 are N.
  • R is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted C6 to C30 aryl; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R is hydrogen; Or deuterium.
  • L1 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • L1 and L2 are each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 15 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • L1 and L2 are each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 15 carbon atoms.
  • L1 and L2 are each independently a direct bond; Or a substituted or unsubstituted phenylene group.
  • R3 is selected from the group consisting of deuterium; A substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or adjacent R3's are bonded to each other to form a ring.
  • R3 when L2 is a direct bond, R3 is a substituted or unsubstituted aryl group or a substituted or unsubstituted heterocyclic group, or adjacent R3 is bonded to each other to form a ring.
  • R3 when L2 is a direct bond, R3 is a substituted or unsubstituted aryl group, or adjacent R3 is bonded to each other to form a ring.
  • R3 when L2 is a direct bond, R3 is a substituted or unsubstituted aryl group, or adjacent R3 is bonded to each other to form a substituted or unsubstituted hydrocarbon ring.
  • R < 3 &gt is a substituted or unsubstituted phenyl group, or adjacent R & .
  • A1 to A3 each independently represent hydrogen; heavy hydrogen; A halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, a1 is an integer of 0 to 4, and * represents a substituted position.
  • R &lt when L2 is a direct bond, R < 3 > is a phenyl group, or adjacent R & .
  • A1 is hydrogen
  • A2 and A3 are each independently a substituted or unsubstituted alkyl group
  • a1 is 4, and * indicates substitution position.
  • A2 and A3 are methyl groups.
  • R 1 is a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R 1 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
  • R 1 is a substituted or unsubstituted phenyl group.
  • R2 and R3 are each independently selected from the group consisting of hydrogen; heavy hydrogen; 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.
  • R2 and R3 are each independently selected from the group consisting of hydrogen; heavy hydrogen; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms or a substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • R2 and R3 are each independently selected from the group consisting of hydrogen; Or deuterium.
  • R2 and R3 are hydrogen.
  • R 3 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
  • R 3 is a substituted or unsubstituted phenyl group.
  • a and b are 0 or 1.
  • adjacent R2 or R3 may combine with each other to form an aromatic hydrocarbon ring.
  • adjacent R2 or R3 may combine with each other to form an aromatic hydrocarbon ring having 4 to 30 carbon atoms.
  • adjacent R2 or R3 may combine with each other to form an aromatic hydrocarbon ring having 4 to 15 carbon atoms.
  • the formula (1) is represented by any one of the following structures.
  • the formula (2) is represented by any one of the following structures.
  • the conjugation length of the compound and the energy band gap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
  • compounds having various energy bandgaps can be synthesized by introducing various substituents into the core structure as described above. Further, in the present invention, the HOMO and LUMO energy levels of the compound can be controlled by introducing various substituents to the core structure having the above structure.
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound of Formula 1 or Formula 2.
  • the organic light emitting device of the present invention can be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic compound layers are formed using the above-described compounds.
  • the compound may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
  • 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 injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer 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 material layer may include an electron transporting layer or an electron injecting layer, and the electron transporting layer or the electron injecting layer may include a compound represented by Formula 1 or Formula 2.
  • the organic material layer may include a hole injecting layer or a hole transporting layer, and the hole injecting layer or the hole transporting layer may include the compound represented by Formula 1 or Formula 2.
  • the organic layer includes a light-emitting layer
  • the light-emitting layer includes a compound represented by the general formula (1) or (2).
  • the organic layer includes a light emitting layer
  • the light emitting layer may include the compound represented by Formula 1 or Formula 2 as a dopant of the light emitting layer.
  • the organic material layer containing the compound represented by the above formula (1) or (2) contains a compound represented by the above formula (1) or (2) as a dopant and includes a fluorescent host or a phosphorescent host.
  • a compound, a metal or a metal compound as a dopant is another embodiment, the organic material layer containing the compound represented by the above formula (1) or (2) contains a compound represented by the above formula (1) or (2) as a dopant and includes a fluorescent host or a phosphorescent host.
  • a compound, a metal or a metal compound as a dopant is a compound represented by the above formula (1) or (2) as a dopant and includes a fluorescent host or a phosphorescent host.
  • the organic material layer containing the compound represented by Formula 1 or Formula 2 includes a compound represented by Formula 1 or Formula 2 as a dopant and includes a fluorescent host or a phosphorescent host, and an iridium-based (Ir ) Dopants.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is a cathode.
  • the structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but the present invention is not limited thereto.
  • FIG. 1 illustrates the structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially laminated on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • FIG. 2 shows an organic light emitting device in which an anode 2, a hole injecting layer 5, a hole transporting layer 6, a light emitting layer 7, an electron transporting layer 8 and a cathode 4 are sequentially laminated on a substrate 1 Structure is illustrated.
  • the compound may be included in the hole injecting layer 5, the hole transporting layer 6, the light emitting layer 7, or the electron transporting layer 8.
  • the organic light emitting device may be formed by using a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate,
  • a PVD (physical vapor deposition) method such as sputtering or e-beam evaporation to form a metal oxide or a metal oxide having conductivity on the substrate
  • an organic material layer including a hole injection layer, a hole transporting layer, a light emitting layer, and an electron transporting layer is formed on the anode, and a material which can be used as a cathode is deposited thereon.
  • an organic light emitting device may be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the organic material layer may have a multi-layer structure including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer, but is not limited thereto and may have a single layer structure.
  • the organic material layer may be formed using a variety of polymeric materials by a method such as a solvent process such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, Layer.
  • the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of 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; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injecting material it is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material is between the work function of the anode material and the HOMO of the surrounding organic layer.
  • the hole injecting material include metal porphyrine, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, perylene , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transporting material a material capable of transporting holes from the anode or the hole injecting layer to the light emitting layer and having high mobility to holes is suitable.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting layer may emit red, green or blue light, and may be formed of a phosphor or a fluorescent material.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Alq 3 8-hydroxy-quinoline aluminum complex
  • Carbazole-based compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compounds
  • Compounds of the benzoxazole, benzothiazole and benzimidazole series Polymers of poly (p-phenylenevinylene) (PPV) series
  • Spiro compounds Polyfluorene, rubrene, and the like, but are not limited thereto.
  • Examples of the host material of the light emitting layer include a condensed aromatic ring derivative or a heterocyclic compound.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • Examples of the heterocycle-containing compounds include carbazole derivatives, dibenzofuran derivatives, Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the iridium complex used as a dopant in the light emitting layer is as follows but is not limited thereto.
  • the electron transporting material a material capable of transferring electrons from the cathode well into the light emitting layer, which is suitable for electrons, is suitable.
  • Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, 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 both-sided emission type, depending on the material used.
  • the filtered solid was dissolved in chloroform and washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and hexane to obtain an intermediate 1A (31.5 g, yield: 49%) as a white solid compound.
  • the filtered solid was dissolved in chloroform and washed twice with water. The organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure. The concentrate was purified through a silica column using chloroform and ethyl acetate to obtain an intermediate 1H (46.3 2, yield: 69%) as a white solid compound.
  • the organic layer was separated, and anhydrous magnesium sulfate was added thereto, followed by stirring, followed by filtration, and the filtrate was distilled under reduced pressure.
  • the concentrated compound was purified through a silica column using chloroform and ethyl acetate to prepare a pale pale green solid compound 6 (10.1 g, 55%).
  • a thin glass substrate coated with ITO (indium tin oxide) at a thickness of 1,300 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, a Fischer Co. product was used as a detergent, and distilled water, which was filtered with a filter of Millipore Co., was used as distilled water.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • the following HI-1 compound was thermally vacuum deposited on the ITO transparent electrode prepared above to a thickness of 50 ⁇ to form a hole injection layer.
  • the following HT-1 compound was thermally vacuum deposited on the hole injection layer to form a hole transport layer, and HT-2 compound was vacuum deposited on the HT-1 vapor deposition layer to a thickness of 50 ⁇ to form an electron blocking layer.
  • Compound 1, the following YGH-1 compound, and phosphorescent dopant YGD-1 prepared in Preparation Example 1 were co-deposited as a light emitting layer on the HT-2 deposited film at a weight ratio of 44:44:12 to form a 400 ⁇ thick light emitting layer.
  • the following ET-1 compound was vacuum deposited to a thickness of 250 ANGSTROM to form an electron transporting layer.
  • the following ET-2 compound and Li were vacuum deposited at a weight ratio of 98: .
  • Aluminum was deposited on the electron injecting layer to a thickness of 1000 to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.7 ⁇ / sec
  • the deposition rate of aluminum was maintained at 2 ⁇ / sec
  • the vacuum degree during deposition was maintained at 1 ⁇ 10 -7 to 5 ⁇ 10 -8 torr Respectively.
  • An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound shown in the following Table 1 was used instead of the Compound 1 of Synthesis Example 1 in Experimental Example 1.
  • An organic light emitting device was prepared in the same manner as in Experimental Example 1, except that the compound shown in the following Table 1 was used instead of the Compound 1 of Synthesis Example 1 in Experimental Example 1.
  • the compounds of CE1 to CE7 in the following Table 1 are as follows.
  • Experimental Example and Comparative an organic light-emitting device of Experimental Example were measured and a voltage efficiency at a current density of 10mA / cm 2, to measure the lifetime at a current density of 50mA / cm 2 and the results are shown in Table 1.
  • LT 95 means the time to reach 95% of the initial luminance.

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  • Spectroscopy & Molecular Physics (AREA)
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  • Electroluminescent Light Sources (AREA)
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Abstract

La présente invention concerne un composé représenté par la formule chimique (1) ou la formule chimique (2) et une diode électroluminescente organique le comprenant.
PCT/KR2019/000903 2018-01-22 2019-01-22 Composé polycyclique et diode électroluminescente organique le comprenant WO2019143224A1 (fr)

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EP4083166A4 (fr) * 2019-12-27 2024-01-24 Nippon Steel Chemical & Mat Co Ltd Matériau destiné à un élément électroluminescent organique, et élément électroluminescent organique

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KR20240065908A (ko) * 2022-11-07 2024-05-14 삼성에스디아이 주식회사 유기 광전자 소자용 화합물, 유기 광전자 소자용 조성물, 유기 광전자 소자 및 표시 장치

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