WO2020080822A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2020080822A1
WO2020080822A1 PCT/KR2019/013580 KR2019013580W WO2020080822A1 WO 2020080822 A1 WO2020080822 A1 WO 2020080822A1 KR 2019013580 W KR2019013580 W KR 2019013580W WO 2020080822 A1 WO2020080822 A1 WO 2020080822A1
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group
substituted
unsubstituted
formula
compound
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김진주
이준엽
홍완표
유지광
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주식회사 엘지화학
성균관대학교산학협력단
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Priority to CN201980030648.4A priority Critical patent/CN112088158B/zh
Publication of WO2020080822A1 publication Critical patent/WO2020080822A1/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
    • 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
    • C07D487/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00
    • C07D487/02—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, not provided for by groups C07D451/00 - C07D477/00 in which the condensed system contains two hetero rings
    • C07D487/04—Ortho-condensed systems
    • 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 the 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 forming an interface 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-layered structure composed of different materials, for example, may be formed of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, and the like.
  • Materials used as the 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 transport materials, and electron injection materials, depending on function.
  • the light-emitting materials include blue, green, and red light-emitting materials depending on the light-emitting color, and yellow and orange light-emitting materials necessary for realizing a better natural 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 small energy band gap and excellent luminous efficiency is mixed with the luminescent layer than the host that mainly constitutes the luminescent layer, excitons generated from the host are transported as a dopant to produce light with high efficiency. 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.
  • a material forming an organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron transport material, an electron injection material, etc., are supported by stable and efficient materials. Development of new materials continues to be required.
  • An exemplary embodiment of the present specification is to provide a compound represented by the formula (1).
  • X is S or O
  • Y1 to Y3 are the same as or different from each other, and each independently, N or CR,
  • At least one of Y1 to Y3 is N,
  • Ar3 is represented by the following formula 2 or 3,
  • R, R1, R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • R2 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted carbazole group, or combines with an adjacent substituent to form a substituted or unsubstituted ring,
  • Ar1, Ar2 and Ar6 are each independently a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring,
  • a is an integer from 0 to 6
  • b is an integer from 1 to 8
  • c and d are each independently an integer from 0 to 4,
  • a to d are each independently 2 or more, the substituents in parentheses are the same or different from each other, and adjacent groups may combine with each other to form a ring.
  • the first electrode A second electrode provided to face the first electrode; And an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer includes the compound.
  • the compounds described herein can be used as a material for an organic material layer of an organic light emitting device.
  • the compound according to at least one embodiment can improve the lifespan characteristics or the organic light emitting device.
  • the compounds described herein can be used as materials such as a light emitting layer, an electron transport layer, an electron injection layer, a hole transport layer, a hole injection layer, and the like.
  • FIG. 1 shows an example of an organic light emitting device including a substrate 1, an anode 2, a light emitting layer 3, and a cathode 4.
  • FIG. 2 shows an anode 2, a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer on the substrate 1
  • An example of an organic light-emitting device comprising (9) and a cathode (4) is shown.
  • the present specification provides a compound represented by Chemical Formula 1.
  • the compound represented by Chemical Formula 1 is used in the organic material layer of the organic light emitting device, the efficiency of the organic light emitting device is always maintained.
  • 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 refers to deuterium; Halogen group; Cyano group; 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, substituted with 1 or 2 or more substituents selected from the group, or substituted with 2 or more substituents among the 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 alkyl group may be a straight chain or a 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, n-propyl group, isopropyl group, n-butyl group, isobutyl group, tert-butyl group, n-pentyl group, n-hexyl group, n-heptyl group, n-ox Tilgi, and the like, but are not limited to these.
  • 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.
  • 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 including the two or more aryl groups may include 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, anthracenylamine group, 3-methyl-phenylamine group, 4-methyl-naphthylamine group, and 2-methyl-biphenylamine Group, 9-methyl-anthracenylamine group, diphenyl amine group, phenyl naphthyl amine group, biphenyl phenyl amine 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 30. According to one embodiment, the carbon number of the aryl group is 6 to 20.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl 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, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may combine with each other to form a spiro structure.
  • Spirofluorenyl groups such as, (9,9-dimethylfluorenyl group), and It may be a substituted fluorenyl group, such as (9,9-diphenylfluorenyl group). However, it is not limited thereto.
  • the heterocyclic group is a heteroatom as a ring group containing at least one of N, O, P, S, Si, and Se, and the number of carbon atoms is not particularly limited, but is preferably 2 to 60 carbon atoms. According to an exemplary embodiment, the heterocyclic group has 2 to 30 carbon atoms.
  • the heterocyclic group include pyridyl group, pyrrol group, pyrimidyl group, pyridazinyl group, furanyl group, thiophenyl group, imidazole group, pyrazole group, dibenzofuranyl group, dibenzothiophenyl group, and the like. It is not limited to.
  • heterocyclic group may be applied, except that the heteroaryl group is aromatic.
  • adjacent A group may mean a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest in conformation to the substituent, or another substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted at the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" to each other.
  • ring is a hydrocarbon ring; Or a heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from examples of the cycloalkyl group or aryl group except for the non-monovalent.
  • the heterocycle is a non-carbon atom, and contains at least one heteroatom, specifically, the heteroatom contains at least one atom selected from the group consisting of N, O, P, S, Si and Se, etc. can do.
  • the heterocycle may be monocyclic or polycyclic, may be aromatic, aliphatic or aromatic and aliphatic condensed ring, and the aromatic heterocycle may be selected from examples of the heteroaryl group except that it is not monovalent.
  • X is S or O.
  • X is S.
  • X is O.
  • At least one of the Y1 to Y3 is N, the rest is CR.
  • Y1 is N
  • Y2 and Y3 is CR.
  • Y2 is N
  • Y1 and Y3 is CR.
  • Y3 is N, Y1 and Y2 is CR.
  • the R, R1, R3 and R4 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxy group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • the R, R1, R3 and R4 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; 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 aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • the R, R1, R3 and R4 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; 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 aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • the R, R1, R3 and R4 are the same as or different from each other, and each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms; 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.
  • the R, R1, R3 and R4 are the same as or different from each other, and each independently, hydrogen; Or deuterium.
  • R2 is a substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted amine group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted carbazole group.
  • R2 is 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 aryl group having 6 to 60 carbon atoms; Or a carbazole group unsubstituted or substituted with an aryl group.
  • R2 is 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 aryl group having 6 to 30 carbon atoms; Or a carbazole group unsubstituted or substituted with an aryl group having 2 to 30 carbon atoms.
  • R2 is a substituted or unsubstituted alkyl group having 1 to 15 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 15 carbon atoms; A substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a carbazole group unsubstituted or substituted with an aryl group having 2 to 15 carbon atoms.
  • R2 is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms; Or a carbazole group unsubstituted or substituted with an aryl group having 2 to 15 carbon atoms.
  • R2 is a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, an anthracene group, a phenanthrene group, a carbazole group, or a carbazole group substituted with a phenyl group.
  • R2 is a phenyl group.
  • R2 is a carbazole group substituted with a phenyl group.
  • R2 is a carbazole group.
  • b is 1.
  • b is 2.
  • b is 3.
  • b is 1, R2 is a substituted or unsubstituted carbazole group.
  • At least one of the R2 is a carbazole group.
  • the R2 is bonded to an adjacent substituent to form a ring.
  • the R2 is bonded to an adjacent substituent to form an aromatic ring.
  • the R2 is bonded to an adjacent substituent to form a hetero ring.
  • b is 2
  • R2 is an adjacent substituent combines to form a ring.
  • b is 2
  • R2 is an adjacent substituent combines to form an aromatic ring.
  • b is 2
  • R2 is an adjacent substituent is bonded to form a hetero ring.
  • Ar1, Ar2, and Ar6 are the same as or different from each other, and each independently, a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heterocyclic group, or combine with an adjacent group to form a ring.
  • Ar1, Ar2, and Ar6 are the same as or different from each other, and each independently, a substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; 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.
  • Ar1, Ar2, and Ar6 are the same as or different from each other, and each independently, 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.
  • Ar1, Ar2, and Ar6 are the same as or different from each other, and each independently, 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.
  • Ar1, Ar2, and Ar6 are the same as or different from each other, and each independently, 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.
  • Ar1, Ar2, and Ar6 are the same as or different from each other, and each independently, a phenyl group, a biphenyl group, a terphenyl group, a naphthyl group, anthracene group, phenanthrene group, triphenylene group, and triazine group , Pyrimidine group, pyridine group, dibenzofuran group, dibenzothiophene group, or carbazole group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group, a biphenyl group, or a dibenzofuran group.
  • Ar6 is a phenyl group.
  • the formula 3 is any one selected from the following formulas 3-1 to 3-3.
  • R3, R4, Ar6, c and d are as described above.
  • the formula 3 is any one selected from the following formulas 3-4 to 3-6.
  • R3, R4, Ar6, c and d are as described above.
  • the formula 1 is represented by any one of the following structures.
  • the number of excitons generated in singlet and triplet is generated at a ratio of 25:75 (single term: triplet), and fluorescent emission, phosphorescence emission, and thermal activation delayed fluorescence depending on the light emission type according to exciton movement It can be divided into luminescence.
  • the phosphorescence it means that the exciton of the triplet excited state moves to the ground state and emits light
  • the exciton of the singlet excited state is the ground state ( It means that it moves to the ground state to emit light
  • the thermally activated delayed fluorescence emission reverses the transition from the triplet excited state to the singlet excited state, and the singlet excited state. It means that the exciton moves to the ground state and causes fluorescence emission.
  • the compound according to the exemplary embodiment of the present specification has phosphorescence emission or thermal activation delayed fluorescence characteristics, and thus, excitons of the triplet excited state are reverse-transitioned to the singlet excited state, and their energy is generally reversed. It can be delivered to the dopant to realize an organic light emitting device having high efficiency.
  • the compound of Formula 1 according to an exemplary embodiment of the present specification may be prepared by a manufacturing method described later.
  • the compound of Formula 1 may have a core structure as shown in the following scheme.
  • Substituents can be combined by methods known in the art, and the type, location or number of substituents can be changed according to techniques known in the art.
  • 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 band gap.
  • compounds having various energy band gaps can be synthesized by introducing various substituents to the core structure as described above.
  • 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 provided to face the first electrode; And one or more organic material layers provided between the first electrode and the second electrode, wherein at least one layer of the organic material layer comprises a compound of Formula 1.
  • the organic light-emitting device of the present invention can be manufactured by a conventional manufacturing method and material of an organic light-emitting device, except that one or more organic material layers are formed using the above-described compound.
  • the compound may be formed as an organic material layer by a solution coating method as well as a vacuum deposition method when manufacturing an organic light emitting device.
  • 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 invention 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 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 as an organic material layer.
  • the structure of the organic light emitting device is not limited to this, and may include fewer organic material layers.
  • the organic material layer may include an electron transport layer or an electron injection layer, and the electron transport layer or electron injection layer may include a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes a compound represented by Chemical Formula 1.
  • the light emitting layer includes a host and a dopant in a mass ratio of 99: 1 to 50:50.
  • the light emitting layer includes a host and a dopant in a mass ratio of 90:10 to 70:30.
  • the emission layer may include a compound represented by Chemical Formula 1 as a dopant.
  • the light emitting layer may include an additional dopant.
  • the light emitting layer may include a metal complex as an additional dopant.
  • the light emitting layer may include an iridium complex as an additional dopant.
  • the light emitting layer may further include a fluorescent dopant.
  • the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and other organic compounds, metals or metal compounds It may include as a dopant.
  • the organic material layer including the compound represented by Chemical Formula 1 includes the compound represented by Chemical Formula 1 as a dopant, includes a fluorescent host or a phosphorescent host, and can be used with an iridium-based (Ir) dopant. There is .
  • 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 structure of the organic light emitting device of the present invention may have a structure as shown in FIGS. 1 and 2, but 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 stacked on a substrate 1.
  • the compound may be included in the light emitting layer (3).
  • 1 is for illustrative purposes only, and may include an additional layer between the anode 2 and the light emitting layer 3 or between the light emitting layer 3 and the cathode 4.
  • an anode 2 on the substrate 1 a hole injection layer 5, a hole transport layer 6, an electron blocking layer 7, a light emitting layer 3, a hole blocking layer 8, an electron injection and transport layer
  • the structure of the organic light emitting element in which (9) and the cathode 4 are sequentially stacked is illustrated.
  • 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 It can be prepared by depositing an anode to form an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • PVD metal vapor deposition
  • 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 use a variety of polymer materials to reduce the number of solvent processes (e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer) rather than deposition. Can be prepared in layers.
  • the positive electrode material is usually a material having a large work function to facilitate hole injection into the 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 and 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 material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof;
  • There is a multilayer structure material such as LiF / Al or LiO 2 / Al, but is not limited thereto.
  • the hole injection material is a material that can be well injected holes from the anode at a low voltage, and it is preferable that the hole injection material has a high occupied molecular orbital (HOMO) between the work function of the anode material and the HOMO of the surrounding organic material layer.
  • HOMO occupied molecular orbital
  • Specific examples of 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.
  • a material capable of receiving holes from an anode or a hole injection layer and transporting holes to a light emitting layer is suitable as 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.
  • 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 light 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 (Alq 3 ); 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.
  • Alq 3 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 host material of the light emitting layer includes a condensed aromatic ring derivative or a heterocyclic compound.
  • condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, fluoranthene compounds, etc.
  • heterocyclic compounds include carbazole derivatives, dibenzofuran derivatives, and ladder types Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • the iridium-based complex used as a dopant in the light emitting layer is as follows, but is not limited thereto.
  • the material used as the fluorescent dopant of the light emitting layer is as follows, but is not limited thereto.
  • the electron transport material a material capable of receiving electrons from the cathode well 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 Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these.
  • 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.
  • the intermediate 1-1 (16.81 g, 73.07 mmol) and 2-chloro-4,6-diphenylpyridine (19.37 g, 73.07 mmol) and tetrakis (triphenylphosphine) palladium (0) 2 mol% of tetrahydrofuran Put it in 210ml, mix with potassium carbonate (30.30g, 219.21mmol) aqueous solution and stir and raise the temperature until reflux. After starting reflux, the reaction was completed after 3 hours, the temperature was lowered to room temperature, concentrated under reduced pressure, and then purified by column to prepare intermediate 9-1 (21.84g, yield 72%).
  • intermediate 11-1 14.86 g, 60.40 mmol
  • 2-chloro-4- (dibenzo [b, d] furan-4-yl) -6-phenyl-1,3,5-triazine 21.57g, 60.40mmol
  • 2 mol% of tetrakis (triphenylphosphine) palladium (0) was added to 180 ml of tetrahydrofuran, mixed with potassium carbonate (25.04 g, 181.20 mmol) aqueous solution, stirred and heated until reflux. After starting to reflux, the reaction was terminated after 5 hours, the temperature was lowered to room temperature, concentrated under reduced pressure, and then purified by column to prepare intermediate 12-1 (18.32g, yield 58%).
  • the intermediate 12-1 (18.32 g, 35.03 mmol), 9,9 ''-diphenyl-9H, 9'H, 9''H-3,3 ': 6', 3 ''-turbazole (22.74 g, 35.03mmol) and sodium hydride (1.68g, 70.06mmol) were added to 110ml of dimethylformamide and heated and stirred. After completion of the reaction after 9 hours, the temperature was lowered to room temperature, concentrated under reduced pressure, and then purified by column to prepare compound 12 (20.18 g, yield 50%).
  • a glass substrate coated with a thin film of ITO (indium tin oxide) at a thickness of 1,000 ⁇ was placed in distilled water in which detergent was dissolved and washed with ultrasonic waves.
  • Fischer Co. was used as a detergent
  • distilled water filtered secondarily by a filter of Millipore Co. was used as distilled water.
  • ultrasonic cleaning was repeated twice for 10 minutes with distilled water.
  • 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 transferred to a vacuum evaporator.
  • a hole transport layer is formed by vacuum-depositing the following compound 4-4'-bis [N- (1-naphthyl) -N-phenylamino] biphenyl (NPB) (300 kPa), which is a material for transporting holes on the hole injection layer. Did.
  • a m-CBP and a compound 1 as shown below were vacuum-deposited at a weight ratio of 70:30 with a thickness of 300 mm 3 over the electron blocking layer to form a light emitting layer.
  • a hole blocking layer was formed by vacuum-depositing the compound HB1 with a thickness of 100 Pa on the light emitting layer.
  • a compound ET1 and a compound LiQ were vacuum-deposited at a weight ratio of 1: 1 to form an electron injection and transport layer with a thickness of 300 MPa.
  • lithium fluoride (LiF) with a thickness of 12 ⁇ and aluminum with a thickness of 2,000 ⁇ were sequentially deposited to form a negative electrode.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the compound of Table 1 below instead of the compound 1 in Example 1.
  • An organic light emitting device was manufactured in the same manner as in Example 1, except that the following compounds T1 to T3 and 4CzIPN were used instead of Compound 1 in Example 1.
  • Example 1 Compound 1 3.8 24.7 (0.33, 0.63)
  • Example 2 Compound 2 4.0 23.1 (0.34, 0.62)
  • Example 3 Compound 3 4.1 22.8 (0.33, 0.63)
  • Example 4 Compound 4 4.1 23.9 (0.33, 0.64)
  • Example 5 Compound 5 4.0 24.7 (0.33, 0.62)
  • Example 6 Compound 6 3.9 23.1 (0.32, 0.63)
  • Example 7 Compound 7 3.9 22.8 (0.33, 0.64)
  • Example 8 Compound 8 3.8 23.4 (0.34, 0.62)
  • Example 9 Compound 9 4.0 22.7 (0.33, 0.64)
  • Example 10 Compound 10 4.1 23.5 (0.33, 0.64)
  • Example 11 Compound 11 3.9 23.7 (0.33, 0.64)
  • Example 12 Compound 12 3.8 24.1 (0.34, 0.62)
  • Example 13 Compound 13 4.0 23.8 (0.33, 0.64)
  • Example 14 Compound 14 3.9 23.
  • the T2 of Comparative Example 2 also reduces steric compared to the present compound due to unsubstituted carbazole.
  • the imidazole was substituted on the p-type carbazole side, and the HOMO distribution range was biased toward the carbazole side, resulting in a decrease in efficiency.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Physics & Mathematics (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 composé représenté par la formule chimique 1 et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/013580 2018-10-16 2019-10-16 Composé et dispositif électroluminescent organique le comprenant WO2020080822A1 (fr)

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