WO2019164218A1 - Composé polycyclique et diode électroluminescente organique le comprenant - Google Patents

Composé polycyclique et diode électroluminescente organique le comprenant Download PDF

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WO2019164218A1
WO2019164218A1 PCT/KR2019/001976 KR2019001976W WO2019164218A1 WO 2019164218 A1 WO2019164218 A1 WO 2019164218A1 KR 2019001976 W KR2019001976 W KR 2019001976W WO 2019164218 A1 WO2019164218 A1 WO 2019164218A1
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group
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정민우
박슬찬
이동훈
장분재
이정하
한수진
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주식회사 엘지화학
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Priority to CN201980007020.2A priority Critical patent/CN111527081B/zh
Publication of WO2019164218A1 publication Critical patent/WO2019164218A1/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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • C07D405/02—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 two hetero rings
    • C07D405/04—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 two hetero rings directly linked by a ring-member-to-ring-member bond
    • 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
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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]
    • H10K50/14—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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    • 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
    • H10K85/6574—Polycyclic condensed heteroaromatic hydrocarbons comprising only oxygen in the heteroaromatic polycondensed ring system, e.g. cumarine dyes
    • 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
    • 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
    • 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]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • an organic light emitting device is a light emitting device using an organic semiconductor material, and requires an exchange of holes and / or electrons between an electrode and the organic semiconductor material.
  • the organic light emitting device can be classified into two types according to the operation principle. First, an exciton is formed in the organic layer by photons introduced into the device from an external light source, and the exciton is separated into electrons and holes, and these electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting element of the form.
  • the second is a light emitting device in which holes and / or electrons are injected into the organic semiconductor material layer that interfaces with the electrodes by applying voltage or current to two or more electrodes, and is operated by the injected electrons and holes.
  • organic light emitting phenomenon refers to a phenomenon of converting 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, a cathode, and an organic material layer therebetween.
  • the organic layer is often composed of a multi-layered structure composed of different materials in order to increase the efficiency and stability of the organic light emitting device, for example, a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer, an electron injection layer, etc. Can lose.
  • organic light emitting devices When the voltage is applied between the two electrodes in the structure of the organic light emitting device, holes are injected into the organic material layer at the anode and electrons are injected into the organic material layer, and excitons are formed when the injected holes and the electrons meet each other. When it falls back to the ground, it glows.
  • organic light emitting devices are known to have characteristics such as self-luminous, high brightness, high efficiency, low driving voltage, wide viewing angle, and high contrast.
  • 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 suppressing materials, electron transport materials, electron injection materials and the like depending on their functions.
  • the luminescent material includes blue, green, and red luminescent materials and yellow and orange luminescent materials necessary to realize better natural colors depending on the emission color.
  • a host / dopant system may be used as the light emitting material in order to increase the light emission efficiency through increase in color purity and energy transfer.
  • the principle is that when a small amount of dopant having a smaller energy band gap and excellent luminous efficiency than the host mainly constituting the light emitting layer is mixed in the light emitting layer, excitons generated in the host are transported to the dopant to give high efficiency light.
  • the wavelength of the host shifts to the wavelength of the dopant, light having a desired wavelength can be obtained according to the type of dopant to be used.
  • a material which constitutes an organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron suppressor, an electron transport material, an electron injection material, etc., is stable and efficient. Backed by, the development of new materials continues to be required.
  • An exemplary embodiment of the present specification provides a compound represented by the following formula (1).
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • X1 to X3 are the same as or different from each other, and each independently N or C (R1), at least 2 is N,
  • W, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • Y is O; S; N (R2); C (R3) (R4); Or C (R5) bonded to L1 or L2,
  • Q1 to Q8 are the same as or different from each other, and each independently N; C (R6); Or C bonded to L1 or L2,
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • n 1 or 2
  • n 1 or 2
  • substituents in parentheses are the same as or different from each other
  • n is an integer of 1 to 5, and when n is 2 or more, the substituents in parentheses are the same as or different from each other.
  • the present invention is a first electrode; A second electrode provided to face the first electrode; And an organic light emitting device comprising at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes the compound described above.
  • the compound described herein can be used as the material of the organic material layer of the organic light emitting device.
  • an organic light emitting device including the compound according to at least one embodiment it is possible to obtain an organic light emitting device having a low driving voltage, high efficiency and long life.
  • FIG. 1 illustrates an example of an organic light emitting device including a substrate 100, an anode 101, a light emitting layer 102, and a cathode 103.
  • FIG. 2 illustrates a substrate 100, an anode 101, a hole injection layer 104, a hole transport layer 105, an electron suppression layer 106, a light emitting layer 102, an electron transport layer 107, and an electron injection layer 108.
  • the organic light emitting element including the cathode 103.
  • the present specification provides a compound represented by the following Formula 1.
  • the efficiency and life characteristics of the organic light emitting device is improved.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • X1 to X3 are the same as or different from each other, and each independently N or C (R1), at least 2 is N,
  • W, Ar1 and Ar2 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • Y is O; S; N (R2); C (R3) (R4); Or C (R5) bonded to L1 or L2,
  • Q1 to Q8 are the same as or different from each other, and each independently N; C (R6); Or C bonded to L1 or L2,
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • n 1 or 2
  • n 1 or 2
  • substituents in parentheses are the same as or different from each other
  • n is an integer of 1 to 5, and when n is 2 or more, the substituents in parentheses are the same as or different from each other.
  • substituted means that a hydrogen atom bonded to a 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 replaced, that is, a position where the substituent can be substituted, if two or more are substituted , Two or more substituents may be the same or different from each other.
  • substituted or unsubstituted is deuterium; Halogen group; Cyano group (-CN); Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; And it is substituted with one or two or more substituents selected from the group consisting of a substituted or unsubstituted heterocyclic group, or two or more of the substituents exemplified above are substituted with a substituent, or means that do not have any substituents.
  • a substituent to which two or more substituents are linked may be a biphenyl group. That is, the biphenyl group may be an aryl group or may be interpreted as a substituent to which two phenyl groups are linked.
  • examples of the halogen group include fluorine (-F), chlorine (-Cl), bromine (-Br) or iodine (-I).
  • carbon number of a carbonyl group in this specification is not specifically limited, It is preferable that it is C1-C40. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the oxygen of the ester group may be substituted with a linear, branched or cyclic alkyl group having 1 to 20 carbon atoms or an aryl group having 6 to 30 carbon atoms. Specifically, it may be a compound of the following structural formula, but is not limited thereto.
  • carbon number of an imide group is not specifically limited, It is preferable that it is C1-C25. Specifically, it may be a compound having a structure as follows, but is not limited thereto.
  • the silyl group may be represented by a chemical formula of -SiY 1 Y 2 Y 3 , wherein Y 1 , Y 2 and Y 3 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • Specific examples of the silyl group include trimethylsilyl group, triethylsilyl group, tert-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, and phenylsilyl group. Do not.
  • the boron group may be represented by a chemical formula of -BY 4 Y 5 , wherein Y 4 and Y 5 are each hydrogen; Substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, a dimethyl boron group, a diethyl boron group, a tert-butylmethylboron group, a diphenyl boron group, a phenylboron group, and the like.
  • the alkyl group may be linear or branched chain, carbon number is not particularly limited, but is preferably 1 to 60. According to an exemplary embodiment, the alkyl group has 1 to 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 are not limited thereto.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to one embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, cyclopropyl 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 preferably has 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to an exemplary embodiment, the aryl group has 6 to 30 carbon atoms. According to an exemplary embodiment, the aryl group has 6 to 20 carbon atoms.
  • the aryl group may be, for example, a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, peryllenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.
  • the fluorenyl group may be substituted, and two substituents may be bonded to 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-diphenyl fluorenyl group).
  • the present invention is not limited thereto.
  • the heterocyclic group is a ring group containing one or more of N, O, P, S, Si, and Se as hetero atoms, and carbon number 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.
  • heterocyclic group examples include, for example, pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazinyl group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group , Carbazole groups, benzocarbazole groups, naphthobenzofuran groups, benzonaphthothiophene groups, indenocarbazole groups and the like, but are not limited thereto.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • adjacent The group may mean a substituent substituted with an atom directly connected to an atom in which the corresponding substituent is substituted, a substituent positioned closest in structural conformation to the substituent, or another substituent substituted in an atom in which the substituent is substituted.
  • 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" to each other.
  • the description of the aryl group described above may be applied except that the arylene group is a divalent group.
  • heteroaryl group described above may be applied except that the heteroarylene group is a divalent group.
  • X1 to X3 are the same as or different from each other, and are each independently N or C (R1), and two or more are N.
  • X1 to X3 are N.
  • Y is O; S; N (R2); C (R3) (R4); Or C (R5) which is bound to L1 or L2.
  • Y is O; S; C (R3) (R4); Or C (R5) bonded to L1 or L2, wherein R3 to R5 are the same as defined in Chemical Formula 1.
  • Chemical Formula 1 may be represented by the following Chemical Formula 2 or 3.
  • X1 to X3, Ar1, Ar2, L1 to L3, R5, W, Y and Q1 to Q8 are the same as defined in Chemical Formula 1.
  • the Q1 to Q8 are the same as or different from each other, and each independently N; C (R6); Or C bound to L1 or L2.
  • the R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Silyl groups; Boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • the R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Silyl groups; Boron 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; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Silyl groups; Boron 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; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • the R1 to R6 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; Halogen group; Cyano group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R1 is hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms.
  • R2 is hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group.
  • R2 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 60 carbon atoms.
  • R2 is hydrogen; heavy hydrogen; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • R2 is an aryl group having 6 to 60 carbon atoms.
  • R2 is hydrogen; heavy hydrogen; Substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted anthracenyl group; Or a substituted or unsubstituted phenanthrenyl group.
  • R2 is hydrogen; heavy hydrogen; Phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Anthracenyl group; Or a phenanthrenyl group.
  • R2 is a phenyl group.
  • 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; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • 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; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • R3 and R4 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms; Or an aryl group having 6 to 30 carbon atoms.
  • R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms.
  • R3 and R4 are the same as or different from each other, and are each independently an alkyl group having 1 to 30 carbon atoms.
  • R3 and R4 are the same as or different from each other, and each independently a substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; Substituted or unsubstituted propyl group; Or a substituted or unsubstituted butyl group.
  • R3 and R4 are methyl groups.
  • R5 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R5 is hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms.
  • R6 is hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroaryl group having 2 to 30 carbon atoms.
  • R6 is hydrogen; heavy hydrogen; An alkyl group having 1 to 30 carbon atoms; Aryl groups having 6 to 30 carbon atoms; Or a heteroaryl group having 2 to 30 carbon atoms.
  • R6 is hydrogen
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 60 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 60 carbon atoms.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group having 6 to 30 carbon atoms; Or a substituted or unsubstituted heteroarylene group having 2 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 60 carbon atoms.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; Or a substituted or unsubstituted arylene group having 6 to 30 carbon atoms.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Or an arylene group having 6 to 30 carbon atoms.
  • the L1 to L3 are the same as or different from each other, and each independently a direct bond; Substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted terphenylene group.
  • L1 to L3 are the same as or different from each other, and each independently a direct bond; Phenylene group; Biphenylene group; Or a terphenylene group.
  • L1 to L3 are the same as or different from each other, and are each independently a direct bond or a phenylene group.
  • W 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.
  • W is a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 60 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a C2-C60 heterocyclic group unsubstituted or substituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
  • W is a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms unsubstituted or substituted with an aryl group having 6 to 30 carbon atoms; Or a heterocyclic group having 2 to 30 carbon atoms unsubstituted or substituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms.
  • W is a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted triphenylenyl group; Substituted or unsubstituted phenanthrenyl group; A substituted or unsubstituted fluorenyl group; Substituted or unsubstituted dibenzofuran group; Substituted or unsubstituted dibenzothiophene group; Substituted or unsubstituted carbazole group; Substituted or unsubstituted pyridine group; Substituted or unsubstituted quinoline group; Or a substituted or unsubstituted indenocarbazole group.
  • W is a phenyl group unsubstituted or substituted with a cyano group, a halogen group, an alkyl group having 1 to 20 carbon atoms, or an aryl group having 6 to 30 carbon atoms;
  • W is a phenyl group unsubstituted or substituted with a cyano group, a fluorine, a methyl group, or a phenyl group;
  • a biphenyl group unsubstituted or substituted with a cyano group, a fluorine, a methyl group or a phenyl group;
  • Terphenyl groups unsubstituted or substituted with a cyano group, a fluorine, a methyl group or a phenyl group;
  • Triphenylenyl group unsubstituted or substituted with a cyano group, a fluorine, a methyl group or a phenyl group;
  • Phenanthrenyl group unsubstituted or substituted with a cyano group,
  • W is a phenyl group unsubstituted or substituted with fluorine or cyano group; Biphenyl group; Terphenyl group; Naphthyl group; Triphenylenyl group; Phenanthrenyl group; 9,9-dimethyl fluorenyl group; Dibenzofuran group; Chibenzo thiophene group; Carbazole groups unsubstituted or substituted with a phenyl group; A pyridine group unsubstituted or substituted with a phenyl group; Quinoline groups; Or an indenocarbazole group substituted with a methyl group.
  • Ar1 and Ar2 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 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 60 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently an aryl group having 6 to 30 carbon atoms.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; Substituted or unsubstituted terphenyl group; Substituted or unsubstituted naphthyl group; Substituted or unsubstituted phenanthrenyl group; Substituted or unsubstituted anthracenyl group; Or a substituted or unsubstituted triphenylenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and each independently a phenyl group; Biphenyl group; Terphenyl group; Naphthyl group; Phenanthrenyl group; Anthracenyl group; Or a triphenylenyl group.
  • Ar1 and Ar2 are the same as or different from each other, and are each independently a phenyl group or a biphenyl group.
  • Ar1 and Ar2 are phenyl groups.
  • any one of Ar 1 and Ar 2 is a phenyl group, and the other is a biphenyl group.
  • m is 1.
  • n is an integer of 1 to 3.
  • n 1 or 2.
  • Formula 1 may be represented by any one of the following compounds.
  • the conjugation length of the compound and the energy bandgap are closely related. Specifically, the longer the conjugation length of the compound, the smaller the energy bandgap.
  • a compound having various energy band gaps can be synthesized by introducing various substituents into the core structure as described above.
  • the HOMO and LUMO energy levels of the compound may be controlled by introducing various substituents into the core structure of the above structure.
  • the compound which has the intrinsic property of the introduced substituent can be synthesize
  • introducing a substituent mainly used in the hole injection layer material, hole transport material, electron suppression material, light emitting layer material and electron transport layer material used in the organic light emitting device manufacturing to the core structure The substance to make can be synthesize
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, wherein at least one of the organic material layers includes a compound represented by Chemical Formula 1 described above.
  • the organic light emitting device of the present invention may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that at least one organic material layer is 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 in the manufacture of the organic light emitting device.
  • the solution coating method means spin coating, dip coating, inkjet printing, screen printing, spraying method, 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 includes a hole injection layer, a hole transport layer, a hole transport layer and a hole injection layer as an organic material layer, an electron suppression layer, a light emitting layer, an electron transport layer and an electron injection layer, an electron transport and an electron injection layer at the same time. , A hole suppression layer or the like.
  • the structure of the organic light emitting device is not limited thereto and may include fewer or more organic layers.
  • 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 the above-described compound.
  • the organic material layer may include a hole injection layer or a hole transport layer, the hole injection layer or a hole transport layer may include the above-described compound.
  • the hole injection layer or the hole transport layer may be made of only the above-described compounds, but the compound may be present in a mixed or doped state with other hole injection layers or hole transport layer materials known in the art.
  • the organic material layer includes a light emitting layer, and the light emitting layer includes the aforementioned compound.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a dopant of the light emitting layer.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the compound described above as a dopant of the light emitting layer and further include a host.
  • the light emitting layer may include a host and a dopant, and the dopant may be included in an amount of 1 wt% to 40 wt% and 1 wt% to 20 wt% with respect to the total weight of the light emitting layer.
  • the organic material layer includes a light emitting layer
  • the light emitting layer includes the compound described above, further includes a fluorescent host or a phosphorescent host, and may include another organic compound, a metal, or a metal compound as a dopant.
  • the compound may be included in 20 to 60% by weight based on the total weight of the light emitting layer
  • the host is 20 to 60% by weight relative to the total weight of the light emitting layer
  • the dopant is 1 to 20% by weight based on the total weight of the light emitting layer May be included as a%.
  • the organic material layer may include a light emitting layer
  • the light emitting layer may include the aforementioned compound as a dopant of the light emitting layer, include a fluorescent host or a phosphorescent host, and may be used with an iridium-based (Ir) dopant.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a host of the light emitting layer.
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the aforementioned compound as a host of the light emitting layer and further include a dopant.
  • the organic material layer may include an electron suppression layer, and the electron suppression layer may include the aforementioned compound.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode and the second electrode is an anode.
  • the organic light emitting diode may have a laminated structure as described below, but is not limited thereto.
  • 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 a structure of an organic light emitting diode in which an anode 101, a light emitting layer 102, and a cathode 103 are sequentially stacked on a substrate 100.
  • the compound may be included in the emission layer 102.
  • the anode 101, the hole injection layer 104, the hole transport layer 105, the electron suppression layer 106, the light emitting layer 102, the electron transport layer 107, and the electron injection layer 108 are disposed on the substrate 100.
  • the compound may be included in the hole injection layer 104, the hole transport layer 105, the light emitting layer 102 or the electron transport layer 107.
  • the organic light emitting device uses a metal vapor deposition (PVD) method such as sputtering or e-beam evaporation, and has a metal oxide or a metal oxide or an alloy thereof on a substrate.
  • PVD metal vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron suppression layer, an electron transport layer and an electron injection layer thereon, and then depositing a material that can be used as a cathode thereon.
  • an organic light emitting device may be manufactured by sequentially depositing a cathode material, an organic material layer, and an anode material on a substrate.
  • the organic material layer includes a hole injection layer, a hole transport layer, a layer for simultaneously injecting and transporting electrons, an electron suppression layer, a light emitting layer, an electron transport layer, an electron injection layer, a layer for simultaneously injecting and transporting electrons, a hole suppression layer, and the like. It may have a multilayer structure, but is not limited thereto and may have a single layer structure.
  • the organic layer may be prepared by using a variety of polymer materials, and by using a method such as spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer, rather than a deposition method. It can be prepared in layers.
  • the anode is an electrode for injecting holes, and a material having a large work function is preferable as an anode material so that hole injection can be smoothly performed into an organic material layer.
  • 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 a metal and an 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, and the like, 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 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; Multilayer structure materials such as LiF / Al or LiO 2 / Al, and the like, but are not limited thereto.
  • the hole injection layer is a layer that facilitates the injection of holes from the anode to the light emitting layer
  • the hole injection material is a material capable of well injecting holes from the anode at a low voltage, the highest occupied hole injection material
  • the molecular orbital is preferably between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • Specific examples of the hole injection material include metal porphyrine, oligothiophene, arylamine-based organics, hexanitrile hexaazatriphenylene-based organics, quinacridone-based organics, and perylene-based Organic substances, anthraquinone and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer may serve to facilitate the transport of holes.
  • a hole transport material a material capable of receiving holes from an anode or a hole injection layer and transferring the holes to a light emitting layer is suitable. Specific examples thereof include an arylamine-based organic material, a conductive polymer, and a block copolymer having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • a hole buffer layer may be additionally provided between the hole injection layer and the hole transport layer, and may include a hole injection or transport material known in the art.
  • An electron suppression layer may be provided between the hole transport layer and the light emitting layer.
  • the electron suppression layer may be a material known in the art, such as arylamine-based organics, carbazole-based organics, and the like.
  • the emission layer may emit red, green, yellow-green, or blue, and may be formed of a phosphor or a fluorescent material.
  • the light emitting material is a material capable of emitting light in the visible region by transporting and combining holes and electrons from the hole transport layer and the electron transport layer, respectively, and a material having good quantum efficiency with respect to fluorescence or phosphorescence is preferable.
  • Specific examples thereof include 8-hydroxyquinoline aluminum complex (Alq 3 ); Carbazole series compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compound; Benzoxazole, benzthiazole and benzimidazole series compounds; Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • Alq 3 8-hydroxyquinoline aluminum complex
  • Carbazole series compounds Dimerized styryl compounds
  • BAlq 10-hydroxybenzoquinoline-metal compound
  • Benzoxazole, benzthiazole and benzimidazole series compounds include Poly (p-phenylenevinylene) (PPV) -based polymers; Spiro compounds; Polyfluorene, rubrene and the like, but are not limited thereto.
  • the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds
  • the heterocyclic containing compounds include carbazole derivatives, dibenzofuran derivatives and ladder types. Furan compounds, pyrimidine derivatives, and the like, but are not limited thereto.
  • light emitting dopants include PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonateiridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium) and PQIr (tris (1-phenylquinoline) iridium Phosphor, such as octaethylporphyrin platinum (PtOEP), or a fluorescent substance such as Alq 3 (tris (8-hydroxyquinolino) aluminum) may be used, but is not limited thereto.
  • the light emitting dopant may be a phosphor such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium) or Alq 3 (tris (8-hydroxyquinolino) aluminum). Fluorescent materials may be used, but are not limited thereto.
  • a light emitting dopant may be a phosphor such as (4,6-F 2 ppy) 2 Irpic, but spiro-DPVBi, spiro-6P, ditylbenzene (DSB) or distriarylene (DSA).
  • a fluorescent material such as PFO-based polymer, PPV-based polymer may be used, but is not limited thereto.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • an electron transporting material a material capable of injecting electrons well from a cathode and transferring the electrons to a light emitting layer is suitable.
  • Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes; Although heterocyclic containing compounds, such as triazine, etc. are mentioned, It is not limited to these.
  • the electron injection layer may play a role of smoothly injecting electrons.
  • As the electron injection material it has the ability of transporting electrons, has an electron injection effect from the cathode, 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 The compound which is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, benzoimidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like Derivatives thereof, metal complex compounds and nitrogen-containing five-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) ( o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtolato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtolato) gallium, It is not limited to this.
  • the hole suppression layer is a layer that blocks the reaching of the cathode of 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 complexes, and the like, but are not limited thereto.
  • the organic light emitting device according to the present invention may be a top emission type, a bottom emission type or a double-sided emission type depending on the material used.
  • the glass substrate coated with ITO (indium tin oxide) having a thickness of 1,300 kPa was put in distilled water in which detergent was dissolved and ultrasonically cleaned.
  • ITO indium tin oxide
  • Fischer Co. was used as a detergent
  • distilled water was filtered secondly as a filter of Millipore Co. as a distilled water.
  • ultrasonic washing was performed twice with distilled water for 10 minutes.
  • ultrasonic washing with a solvent of isopropyl alcohol, acetone, methanol dried and transported to a plasma cleaner.
  • the substrate was cleaned for 5 minutes using an oxygen plasma, and then the substrate was transferred to a vacuum evaporator.
  • the following HI-1 compound was thermally vacuum deposited to a thickness of 50 kPa to form a hole injection layer.
  • a hole transport layer was formed by thermal vacuum evaporation of the following HT-1 compound to a thickness of 250 kPa on the hole injection layer, and an electron suppression layer was formed by vacuum evaporation of the following HT-2 compound to 50 kW on the HT-1 deposition film.
  • Compound 1, the following YGH-1 compound, and phosphorescent dopant YGD-1, which were prepared in Synthesis Example as a light emitting layer on the HT-2 deposited film, were co-deposited at a weight ratio of 44:44:12 to form a light emitting layer having a thickness of 400 kHz.
  • ET-1 compound was vacuum deposited to a thickness of 250 kPa on the light emitting layer to form an electron transport layer
  • the following ET-2 compound and Li were vacuum deposited on the electron transport layer at a weight ratio of 98: 2 to form an electron injection layer having a thickness of 100 kW.
  • Aluminum was deposited on the electron injection layer to a thickness of 1000 ⁇ to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 ⁇ 0.7 ⁇ / sec
  • the aluminum was maintained at the deposition rate of 2 ⁇ / sec
  • the vacuum during deposition was maintained at 1 ⁇ 10 -7 ⁇ 5 ⁇ 10 -8 torr It was.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 of Synthesis Example 1 in Experimental Example 1.
  • An organic light emitting diode was manufactured according to the same method as Experimental Example 1 except for using the compound described in Table 1 below instead of compound 1 of Synthesis Example 1 in Experimental Example 1.
  • the compounds of CE1 to CE6 in 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.
  • LT95 means a time of 95% of the initial luminance.

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Abstract

La présente invention concerne un composé de formule chimique 1 et une diode électroluminescente organique le comprenant.
PCT/KR2019/001976 2018-02-23 2019-02-19 Composé polycyclique et diode électroluminescente organique le comprenant WO2019164218A1 (fr)

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JP2021521254A (ja) * 2018-08-22 2021-08-26 エルジー・ケム・リミテッド 新規な化合物およびこれを利用した有機発光素子
DE102021132671A1 (de) 2020-12-11 2022-06-15 Beijing Summer Sprout Technology Co., Ltd. Organisches Elektrolumineszenzmaterial und Vorrichtung daraus
WO2024038029A1 (fr) * 2022-08-17 2024-02-22 Merck Patent Gmbh Matériaux pour dispositifs électroluminescents organiques

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KR102536248B1 (ko) 2017-06-21 2023-05-25 삼성디스플레이 주식회사 헤테로시클릭 화합물 및 이를 포함한 유기 발광 소자
KR102536246B1 (ko) * 2018-03-23 2023-05-25 삼성디스플레이 주식회사 헤테로고리 화합물 및 이를 포함한 유기 발광 소자
CN112125892B (zh) * 2020-09-01 2023-08-25 烟台显华化工科技有限公司 一种化合物、电子传输材料和有机电致发光器件

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