WO2020138964A1 - Composé et élément électroluminescent organique le comprenant - Google Patents

Composé et élément électroluminescent organique le comprenant Download PDF

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WO2020138964A1
WO2020138964A1 PCT/KR2019/018487 KR2019018487W WO2020138964A1 WO 2020138964 A1 WO2020138964 A1 WO 2020138964A1 KR 2019018487 W KR2019018487 W KR 2019018487W WO 2020138964 A1 WO2020138964 A1 WO 2020138964A1
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substituted
group
unsubstituted
light emitting
compound
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PCT/KR2019/018487
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English (en)
Korean (ko)
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김명곤
홍완표
서상덕
금수정
김경희
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주식회사 엘지화학
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Priority to CN201980076088.6A priority Critical patent/CN113166176B/zh
Publication of WO2020138964A1 publication Critical patent/WO2020138964A1/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
    • H10K85/658—Organoboranes
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • C07F5/027—Organoboranes and organoborohydrides
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F5/00—Compounds containing elements of Groups 3 or 13 of the Periodic Table
    • C07F5/02—Boron compounds
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present specification relates to a compound and an organic light emitting device including the same.
  • the organic light emitting device is a light emitting device using an organic semiconductor material, and requires exchange of holes and/or electrons between the electrode and the organic semiconductor material.
  • the organic light emitting device can be roughly divided into two types according to the operation principle. First, excitons are formed in the organic layer by photons introduced into the device from an external light source, and the excitons are separated into electrons and holes, and the electrons and holes are transferred to different electrodes to be used as current sources (voltage sources). It is a light emitting device of the form.
  • the second is a light emitting device in which holes and/or electrons are injected into a layer of an organic semiconductor material that interfaces with an electrode by applying voltage or current to two or more electrodes, and operated by the injected electrons and holes.
  • the organic light emitting phenomenon refers to a phenomenon that converts electrical energy into light energy using an organic material.
  • An organic light emitting device using an organic light emitting phenomenon usually has a structure including an anode and a cathode and an organic material layer therebetween.
  • the organic material layer is often composed of a multi-layered structure composed of different materials, 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.
  • 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 suppression materials, electron transport materials, and electron injection materials, depending on their function.
  • the light emitting materials include blue, green, and red light emitting materials, and yellow and orange light emitting materials necessary for realizing a better natural color depending on the light emitting color.
  • a host/dopant system may be used as a light emitting material to increase color purity and increase light emission efficiency through energy transfer.
  • the principle is that when a small amount of a dopant having a smaller energy band gap and higher luminous efficiency is mixed with a light emitting layer than a host mainly constituting the light emitting layer, exciton generated from the host is transported as a dopant to produce high efficiency light. At this time, since the wavelength of the host moves to the wavelength of the dopant, light of a desired wavelength can be obtained according to the type of the dopant used.
  • materials constituting an organic material layer in the device such as a hole injection material, a hole transport material, a light emitting material, an electron suppressing material, an electron transport material, an electron injection material, are stable and efficient materials It is supported by, and the development of new materials continues to be required.
  • Described herein is a compound and an organic light emitting device comprising the same.
  • One embodiment of the present specification provides a compound represented by the following Chemical Formula 1.
  • X1 and X2 are each independently NR, O or S,
  • R1 and R2 are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl 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,
  • R is 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,
  • R' is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • a and b are each independently an integer from 0 to 4,
  • x is an integer from 1 to 3
  • y is an integer from 0 to 2
  • Another exemplary embodiment 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, and at least one layer of the organic material layer provides an organic light emitting device including the above-described compound.
  • the compound represented by Chemical Formula 1 of the present invention can be used as a material for the organic material layer of the organic light emitting device.
  • an organic light emitting device including the compound represented by Formula 1 of the present invention When an organic light emitting device including the compound represented by Formula 1 of the present invention is manufactured, an organic light emitting device having high efficiency, low voltage and long life characteristics can be obtained.
  • FIG. 1 shows a structure of an organic light emitting device according to an exemplary embodiment.
  • Figure 2 shows the structure of an organic light emitting device according to another embodiment.
  • substitution means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the position to be substituted is not limited to a position where the hydrogen atom is substituted, that is, a position where the substituent is substitutable, and when two or more are substituted , 2 or more substituents may be the same or different from each other.
  • substituted or unsubstituted in this specification is deuterium (-D); Halogen group; Nitrile group; Nitro group; Hydroxy group; Boron group; Alkoxy groups; Alkyl groups; Cycloalkyl group; Aryl group; And 1 or 2 or more substituents selected from the group consisting of heterocyclic groups, or substituted with two or more substituents among the above-described 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 boron group may be represented by the formula -BY d Y e , wherein Y d and Y e are each hydrogen; A substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group.
  • the boron group may include, but is not limited to, trimethyl boron group, triethyl boron group, tert-butyl dimethyl boron group, triphenyl boron group, phenyl boron group, and the like.
  • the alkyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 1 to 60. According to one embodiment, the alkyl group has 1 to 30 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 20 carbon atoms. According to another exemplary embodiment, the alkyl group has 1 to 10 carbon atoms.
  • alkyl group examples include methyl group, ethyl group, propyl group, n-propyl group, isopropyl group, butyl group, n-butyl group, isobutyl group, tert-butyl group, pentyl group, n-pentyl group, hexyl group, n -Hexyl group, heptyl group, n-heptyl group, octyl group, n-octyl group, and the like, but is not limited to these.
  • the alkenyl group may be straight chain or branched chain, and carbon number is not particularly limited, but is preferably 2 to 30.
  • Specific examples include vinyl, 1-propenyl, isopropenyl, 1-butenyl, 2-butenyl, 3-butenyl, 1-pentenyl, 2-pentenyl, 3-pentenyl, 3-methyl-1- Butenyl, 1,3-butadienyl, allyl, 1-phenylvinyl-1-yl, 2-phenylvinyl-1-yl, 2,2-diphenylvinyl-1-yl, 2-phenyl-2-( Naphthyl-1-yl)vinyl-1-yl, 2,2-bis(diphenyl-1-yl)vinyl-1-yl, steelbenyl group, styrenyl group, and the like, but are not limited thereto.
  • the alkynyl group may be a straight chain or a branched chain, and the number of carbon atoms is not particularly limited, but is preferably 2 to 30. Specific examples include ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl, octynyl, and nonynyl. And the like, but is not limited thereto.
  • the alkoxy group may be a straight chain, branched chain or cyclic chain.
  • the number of carbon atoms of the alkoxy group is not particularly limited, but is preferably 1 to 20 carbon atoms.
  • Substituents comprising alkyl, alkoxy, and other alkyl group moieties described herein include both straight-chain or ground forms.
  • the cycloalkyl group is not particularly limited, but preferably has 3 to 60 carbon atoms, and according to an exemplary embodiment, the cycloalkyl group has 3 to 30 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 20 carbon atoms. According to another exemplary embodiment, the cycloalkyl group has 3 to 6 carbon atoms. Specifically, a cyclopropyl group, cyclobutyl group, cyclopentyl group, cyclohexyl group, cycloheptyl group, cyclooctyl group, and the like, but is not limited thereto.
  • the aryl group is not particularly limited, but is preferably 6 to 60 carbon atoms, and may be a monocyclic aryl group or a polycyclic aryl group. According to one embodiment, the carbon number of the aryl group is 6 to 39. According to one embodiment, the carbon number of the aryl group is 6 to 30.
  • the aryl group may be a phenyl group, a biphenyl group, a terphenyl group, a quarterphenyl group, etc., as a monocyclic aryl group, but is not limited thereto.
  • the polycyclic aryl group may be a naphthyl group, anthracenyl group, phenanthrenyl group, pyrenyl group, perylenyl group, triphenyl group, chrysenyl group, fluorenyl group, triphenylenyl group, etc., but is not limited thereto. no.
  • the fluorene group may be substituted, and two substituents may combine with each other to form a spiro structure.
  • Spirofluorene groups such as (9,9-dimethylfluorene group
  • It may be a substituted fluorene group such as (9,9-diphenylfluorene group).
  • substituted fluorene group such as (9,9-diphenylfluorene group
  • the heterocyclic group is a 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 number of carbon atoms in the heterocyclic group is 2 to 36.
  • heterocyclic group examples include pyridine group, pyrrole group, pyrimidine group, quinoline group, pyridazine group, furan group, thiophene group, imidazole group, pyrazole group, dibenzofuran group, dibenzothiophene group, Carbazole group, benzocarbazole group, benzonaphthofuran group, benzonaphthothiophene group, indenocarbazole group, indolocarbazole group, and the like, but are not limited thereto.
  • heterocyclic group may be applied, except that the heteroaryl group is aromatic.
  • heteroarylene group is a divalent aromatic group.
  • the amine group is -NH 2 ; Alkylamine groups; N-alkylarylamine group; Arylamine group; N-aryl heteroarylamine group; It may be selected from the group consisting of N-alkylheteroarylamine groups and heteroarylamine groups, and the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine group, dimethylamine group, ethylamine group, diethylamine group, phenylamine group, naphthylamine group, biphenylamine group, anthracenylamine group, and 9-methyl-anthracenylamine group , Diphenylamine group, N-phenylnaphthylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group, N-phenylnaphthylamine group, N-bi Phenylnaphthylamine group, N-naphthylfluorenylamine group, N-phenylphenanthrenylamine group, N-biphenylphenanthrenylamine group, N-phenylfluorenylamine group, N-phenylterphenylamine Group, N-phenanthrenylfluorenylamine group,
  • the N-alkylarylamine group means an amine group in which N of an amine group is substituted with an alkyl group and an aryl group.
  • the N-aryl heteroarylamine group means an amine group in which an aryl group and a heteroaryl group are substituted with N of the amine group.
  • the N-alkylheteroarylamine group means an amine group in which an alkyl group and a heteroaryl group are substituted with N of the amine group.
  • the alkyl group, the aryl group, and the heteroaryl group in the N-alkylheteroarylamine group and the heteroarylamine group can be cited in the description of the alkyl group, aryl group, and heteroaryl group, respectively.
  • aryloxy groups include phenoxy group, p-toryloxy group, m-toryloxy group, 3,5-dimethyl-phenoxy group, 2,4,6-trimethylphenoxy group, p-tert-butylphenoxy group, 3- Biphenyloxy group, 4-biphenyloxy group, 1-naphthyloxy group, 2-naphthyloxy group, 4-methyl-1-naphthyloxy group, 5-methyl-2-naphthyloxy group, 1-anthryloxy group , 2-anthryloxy group, 9-anthryloxy group, 1-phenanthryloxy group, 3-phenanthryloxy group, 9-phenanthryloxy group, and the like.
  • the “adjacent” group refers to a substituent substituted on an atom directly connected to an atom in which the substituent is substituted, a substituent positioned closest to the substituent and the other substituent substituted on the atom in which the substituent is substituted.
  • two substituents substituted in the ortho position on the benzene ring and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • ring is a hydrocarbon ring; Or a hetero ring.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and a description of the cycloalkyl group or aryl group may be applied except that the divalent group.
  • heterocyclic group may be applied to the heterocycle except that it is divalent.
  • X1 and X2 are each independently NR, O, or S.
  • X1 and X2 are the same as or different from each other.
  • X1 and X2 is O.
  • X1 and X2 is S.
  • X1 and X2 are each independently, NR.
  • X1 and X2 are each independently, NR, and R is a substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • X1 and X2 are each independently, NR, and R is a substituted or unsubstituted cycloalkyl group; Or a substituted or unsubstituted aryl group.
  • X1 and X2 are each independently NR, and R is a substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • X1 and X2 are each independently NR, and R is a substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • X1 and X2 are each independently NR, and R is a substituted or unsubstituted cycloalkyl group having 3 to 20 carbon atoms; Or a substituted or unsubstituted aryl group having 6 to 20 carbon atoms.
  • R1 and R2 are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring.
  • R1 and R2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring.
  • R1 and R2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group having 1 to 60 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 60 carbon atoms; A substituted or unsubstituted aryl group having 6 to 60 carbon atoms; Or it may be a substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms, or may be combined with adjacent groups to form a substituted or unsubstituted ring.
  • R1 and R2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; A substituted or unsubstituted cycloalkyl group having 3 to 30 carbon atoms; A substituted or unsubstituted aryl group having 6 to 30 carbon atoms; Or it may be a substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms, or may be combined with adjacent groups to form a substituted or unsubstituted ring.
  • R1 and R2 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted amine group; 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, or may be combined with adjacent groups to form a substituted or unsubstituted ring.
  • R is 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.
  • R 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 substituted or unsubstituted heterocyclic group having 2 to 60 carbon atoms.
  • R 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 substituted or unsubstituted heterocyclic group having 2 to 30 carbon atoms.
  • R 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 substituted or unsubstituted heterocyclic group having 2 to 15 carbon atoms.
  • Y1 is O.
  • Y1 is S.
  • R' is a substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • R' is 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.
  • R' is a substituted or unsubstituted alkyl group having 1 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.
  • R' is a substituted or unsubstituted alkyl group having 1 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.
  • R' is a substituted or unsubstituted aryl group having 6 to 60 carbon atoms.
  • a and b are each independently an integer of 2 or more
  • the substituents in parentheses are the same or different from each other, and groups adjacent to each other may combine to form a substituted or unsubstituted ring. That is, a plurality of R1 or R2 may be combined with each other R1 or R2 to form a ring, or R1 and R2 may combine with each other to form a ring.
  • R1 and R2 each independently combine with an adjacent group to form a substituted or unsubstituted ring, a direct bond; Alternatively, any one of the following structures may be formed.
  • A1 to A24 are each independently hydrogen; heavy hydrogen; 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 to a11 are each an integer from 0 to 4,
  • a12 is an integer from 0 to 6
  • the formula 1 is represented by the following formula 2 or 3.
  • R3 to R6 are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl 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,
  • c and d are each independently an integer from 0 to 4,
  • e and f are each independently an integer from 0 to 3
  • R10 to R13 are each independently hydrogen; heavy hydrogen; Halogen group; 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,
  • R14 to R16 are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group,
  • X1, X2, Y1, R', x and y are as in the formula (1).
  • R3 to R6 are each independently hydrogen; heavy hydrogen; Halogen group; A substituted or unsubstituted amine group; A substituted or unsubstituted boron group; A substituted or unsubstituted alkyl group; A substituted or unsubstituted alkenyl group; A substituted or unsubstituted alkynyl group; A substituted or unsubstituted alkoxy group; A substituted or unsubstituted aryloxy group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted aryl group; Or it may be a substituted or unsubstituted heterocyclic group, or may combine with an adjacent group to form a substituted or unsubstituted ring.
  • R3 to R6 are each independently, hydrogen; heavy hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group having 1 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.
  • R3 to R6 are each independently hydrogen; heavy hydrogen; A substituted or unsubstituted amine group; A substituted or unsubstituted alkyl group having 1 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.
  • R3 to R6 are each independently, hydrogen; heavy hydrogen; It is a substituted or unsubstituted aryl group having 6 to 15 carbon atoms.
  • R10 to R13 are 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 may combine with an adjacent group to form a substituted or unsubstituted ring.
  • R10 to R13 are each independently, a substituted or unsubstituted alkyl group; Or it may be a substituted or unsubstituted aryl group, or may combine with an adjacent group to form a substituted or unsubstituted ring.
  • R10 to R13 are each independently, a substituted or unsubstituted alkyl group having 1 to 30 carbon atoms; Or it may be a substituted or unsubstituted aryl group having 6 to 30 carbon atoms, or may be combined with adjacent groups to form a substituted or unsubstituted ring.
  • R14 to R16 are each independently, a substituted or unsubstituted aryl group.
  • R14 to R16 are each independently, a substituted or unsubstituted aryl group having 6 to 30 carbon atoms.
  • the substituents in parentheses are the same or different from each other, and groups adjacent to each other may combine to form a substituted or unsubstituted ring.
  • a plurality of R3, a plurality of R4, a plurality of R5 or a plurality of R6 may form a ring by combining R3, R4, R5 or R6 with each other.
  • R3 to R6 are each independently bonded to an adjacent group to form a substituted or unsubstituted ring, a direct bond; Alternatively, any one of the following structures may be formed.
  • A1 to A12 and A20 to A24 are each independently hydrogen; heavy hydrogen; 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 to a11 are each an integer from 0 to 4,
  • a12 is an integer from 0 to 6
  • a compound not containing naphthalene among the compounds represented by the formula (1) has a delayed fluorescence property of less than ⁇ E st 0.25eV.
  • the number of excitons generated in the singlet and triplet in a general organic light emitting device is generated at a ratio of 25:75 (single term: triplet), and the fluorescent emission, phosphorescence emission, and thermal activation delayed fluorescence depending on the emission type according to exciton movement It can be divided into luminescence.
  • the thermally activated delayed fluorescence represents a phenomenon using a phenomenon of reverse intersystem crossing (RISC) from triplet exciton to singlet exciton, which is also referred to as Thermally Activated Delayed Fluorescence (TADF).
  • RISC reverse intersystem crossing
  • TADF Thermally Activated Delayed Fluorescence
  • naphthalene has a delayed fluorescence property of less than ⁇ E st 0.25 eV, so that excitons in a triplet excited state are typically singlet excited state. It is possible to implement an organic light emitting device having high efficiency by transferring the energy to the dopant by inverse transitioning.
  • the electron pull effect and the tetrahedral structure further reduce the half-width, increasing the distance between the material and the material to prevent stacking, thereby suppressing triplet-polaron quenching. It can increase the efficiency, tune the desired wavelength, form a rigid structure (Rigid form) and increase the safety of the material.
  • the formula 1 may be represented by any one of the following compounds.
  • 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 adjusted by introducing various substituents to the core structure having the above structure.
  • the organic light emitting device includes a first electrode; A second electrode provided to face the first electrode; And at least one organic material layer provided between the first electrode and the second electrode, and at least one layer of the organic material layer comprises the above-described compound.
  • the organic light emitting device of the present specification may be manufactured by a conventional method and material for manufacturing an organic light emitting device, except that one or more organic material layers are formed using the compound represented by Chemical Formula 1 above.
  • an organic light emitting device having an organic material layer formed of the compound represented by the compound 1 it may be formed into an organic material layer by a solution coating method as well as a vacuum deposition method.
  • the solution application method means spin coating, dip coating, inkjet printing, screen printing, spraying, roll coating, and the like, but is not limited to these.
  • the organic material layer of the organic light emitting device of the present specification may have a single-layer structure, but may have a multi-layer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention is a hole transport layer, a hole injection layer, an electron blocking layer, a layer simultaneously performing hole transport and hole injection, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron transport and injection simultaneously as an organic material layer It may have a structure including one or more of the layers.
  • the structure of the organic light emitting device of the present specification is not limited to this, and may include fewer or more organic material layers.
  • the organic material layer includes an electron blocking layer, a hole injection layer, or a hole transport layer, and the electron blocking layer, a hole injection layer, or a hole transport layer includes a compound represented by Chemical Formula 1.
  • the organic material layer includes a hole blocking layer, an electron injection layer, or an electron transport layer, and the hole blocking layer, an electron injection layer, or an electron transport layer includes a compound represented by Chemical Formula 1.
  • the organic material layer includes a light emitting layer, and the light emitting layer may include a compound represented by Chemical Formula 1 described above.
  • the organic material layer includes a light emitting layer
  • the light emitting layer may include the compound represented by Chemical Formula 1 as a dopant in the light emitting layer.
  • the organic material layer includes a dopant comprising a compound represented by Formula 1 described above; And a host.
  • the weight ratio of the host and the dopant is 90: 10 or more, 91:9 or more, 92:8 or more, 93:7 or more, 94:6 or more, 95:5 or more, 96:4 or more, 97 :3 or more, or 98:2 or more, 99.9:0.1 or less, 99.8:0.2 or less, 99.7:0.3 or less, 99.6:0.4 or less, 99.5:0.5 or less, 99.4:0.6 or less, 99.3:0.7 or less, 99.2:0.8 or less , 99.1:0.9 or less, or 99:1 or less.
  • the organic material layer further includes one or two or more layers selected from the group consisting of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer, a hole blocking layer, and an electron blocking layer. do.
  • the first electrode is an anode
  • the second electrode is a cathode
  • the first electrode is a cathode
  • the second electrode is an anode
  • the organic light emitting device may have, for example, a stacked structure as described below, but is not limited thereto.
  • the structure of the organic light emitting device of the present specification may have a structure as shown in FIGS. 1 and 2, but is not limited thereto.
  • FIG. 1 illustrates a structure of an organic light emitting device in which an anode 2, a light emitting layer 3, and a cathode 4 are sequentially stacked on a substrate 1.
  • the compound may be included in the light emitting layer 3.
  • FIG. 2 the anode 2 on the substrate 1, the hole injection layer 5, the hole transport layer 6, the electron blocking layer 7, the light emitting layer 3, the first electron transport layer 8-1, the second
  • the structure of the organic light emitting device in which the electron transport layer 8-2 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
  • PVD metal vapor deposition
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, an electron blocking layer, an electron transport layer and an electron injection layer, and then depositing a material that can be used as a cathode thereon Can be.
  • an organic light emitting device may be made by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the organic material layer may be a multi-layer structure including a hole injection layer, a hole transport layer, an electron injection and electron transport layer, an electron blocking layer, a light emitting layer and an electron transport layer, an electron injection layer, an electron injection and electron transport layer, and the like. However, it is not limited thereto, and may be a single-layer structure. In addition, 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.
  • solvent processes e.g., spin coating, dip coating, doctor blading, screen printing, inkjet printing, or thermal transfer
  • the positive electrode is an electrode for injecting holes
  • a positive electrode material is preferably a material having a large work function to facilitate hole injection into an organic material layer.
  • Specific examples of the positive electrode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); A combination of metal and oxide such as ZnO: Al or SnO 2 : Sb; Conductive polymers such as poly(3-methylthiophene), poly[3,4-(ethylene-1,2-dioxy)thiophene] (PEDOT), polypyrrole, and polyaniline, but are not limited thereto.
  • the cathode is an electrode for injecting electrons
  • the cathode material is preferably a material having a small work function to facilitate electron injection into an organic material layer.
  • the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof;
  • There is a multilayer structure material such as LiF/Al or LiO 2 /Al, but is not limited thereto.
  • the hole injection layer is a layer that serves to smoothly inject holes from the anode to the light emitting layer.
  • a hole injection material can be well injected with holes from the anode at a low voltage, and HOMO (highest occupied) of the hole injection material It is preferable that the molecular orbital is between the work function of the positive electrode material and the HOMO of the surrounding organic material layer.
  • the hole injection material include metal porphyrine, oligothiophene, arylamine-based organic substances, hexanitrile hexaazatriphenylene-based organic substances, quinacridone-based organic substances, and perylene-based substances.
  • the hole injection layer may have a thickness of 1 to 150 nm.
  • the thickness of the hole injection layer is 1 nm or more, there is an advantage of preventing the hole injection characteristics from being deteriorated. If it is 150 nm or less, the thickness of the hole injection layer is too thick, so that the driving voltage is increased to improve hole movement. There is an advantage that can be prevented.
  • the hole transport layer may serve to facilitate the transport of holes.
  • a hole transport material a material capable of receiving holes from an anode or a hole injection layer and transferring them to the light emitting layer is suitable for a material having high mobility for holes.
  • Specific examples include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion, but are not limited thereto.
  • An electron blocking layer may be provided between the hole transport layer and the light emitting layer.
  • the electron blocking layer may be a material known in the art.
  • the light emitting layer may emit red, green, or blue light, and may be made of a phosphorescent material or a fluorescent material.
  • a material capable of emitting light in the visible 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.
  • the organic light emitting diode according to the exemplary embodiment of the present specification includes a light emitting layer, and the light emitting layer includes a compound represented by Formula 1 and a compound represented by Formula H below.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted arylene group; Or a substituted or unsubstituted heteroarylene group,
  • R21 to R27 are the same as or different from each other, and each independently hydrogen; heavy hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; A substituted or unsubstituted silyl group; A substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heteroaryl group,
  • a 0 or 1.
  • the position of -L23-Ar23 is connected to hydrogen or deuterium.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted C6-C30 arylene group; Or a substituted or unsubstituted C2-C30 heteroarylene group containing N, O, or S.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; C6-C30arylene group; Or a C2-C30 heteroarylene group containing N, O, or S, wherein the arylene group or heteroarylene group is substituted or unsubstituted with a C1-C10 alkyl group, a C6-C30 aryl group, or a C2-C30 heteroaryl group. Is bright.
  • L21 to L23 are the same as or different from each other, and each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; A substituted or unsubstituted divalent dibenzofuran group; Or a substituted or unsubstituted divalent dibenzothiophene group.
  • Ar21 to Ar23 are the same or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group; Or a substituted or unsubstituted C2-C30 heteroaryl group.
  • Ar21 to Ar23 are the same or different from each other, and each independently a substituted or unsubstituted C6-C30 aryl group with deuterium; Or a C2-C30 heteroaryl group unsubstituted or substituted with deuterium.
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted monocyclic to 4 ring aryl group; Or a substituted or unsubstituted monocyclic to 4 ring heteroaryl group.
  • Ar21 to Ar23 are the same as or different from each other, and each independently a substituted or unsubstituted deuterium monocyclic to 4 ring aryl group; Or a monocyclic to 4 ring heteroaryl group unsubstituted or substituted with deuterium.
  • Ar21 to Ar23 are the same as or different from each other, and each independently substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted anthracene group; A substituted or unsubstituted phenanthryl group; A substituted or unsubstituted phenylene group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted benzofluorenyl group; A substituted or unsubstituted furan group; A substituted or unsubstituted thiophene group; A substituted or unsubstituted dibenzofuran group; A substituted or unsubstituted naphthobenzofuran group; A substituted or unsubstituted
  • Ar21 and Ar22 are different from each other.
  • Ar21 is a substituted or unsubstituted aryl group
  • Ar22 is a substituted or unsubstituted aryl group
  • Ar21 is a substituted or unsubstituted aryl group
  • Ar22 is a substituted or unsubstituted heteroaryl group.
  • Ar21 is an aryl group unsubstituted or substituted with deuterium
  • Ar22 is an aryl group unsubstituted or substituted with deuterium
  • Ar21 is an aryl group unsubstituted or substituted with deuterium
  • Ar22 is a heteroaryl group unsubstituted or substituted with deuterium.
  • R21 to R27 are the same as or different from each other, and each independently hydrogen or deuterium.
  • R21 to R27 are hydrogen.
  • R21 to R27 are deuterium.
  • Chemical Formula H is represented by the following Chemical Formula H01 or H02.
  • L21 to L23 and Ar21 to Ar23 are as defined in Formula H, D means deuterium, k1 is 0 to 8, and k2 is an integer from 0 to 7.
  • the compound represented by Chemical Formula H is any one selected from the following compounds.
  • the organic light emitting device includes a light emitting layer, the light emitting layer includes a compound represented by Formula 1 as a dopant in the light emitting layer, and a compound represented by Formula H as a host of the light emitting layer.
  • the content of the compound represented by Formula 1 is 0.01 parts by weight to 30 parts by weight; 0.1 to 20 parts by weight; Or 0.5 to 10 parts by weight.
  • the compound represented by Chemical Formula H may be included as one type in the organic material layer (specifically, the light emitting layer), or may be included as two or more types. Specifically, the first host represented by Chemical Formula H and the second host represented by Chemical Formula H may be included in the organic material layer.
  • the weight ratio of the first host represented by Chemical Formula H and the second host represented by Chemical Formula H is 95:5 to 5:95, more preferably 30:70 to 70:30.
  • the first host and the second host are different from each other.
  • the light emitting layer includes one or two or more compounds represented by Formula H.
  • the light emitting layer including the compound represented by Chemical Formula 1 and the compound represented by Chemical Formula H has a blue color.
  • the organic light emitting diode includes two or more light emitting layers, and at least one of the two or more light emitting layers includes a compound represented by Formula 1 and a compound represented by Formula H.
  • the light emitting layer including the compound represented by Formula 1 and the compound represented by Formula H has a blue color, and the light emitting layer not containing the compound represented by Formula 1 and the compound represented by Formula H is blue known in the art, Red or green light-emitting compounds.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • the electron transporting material a material capable of receiving electrons well from the cathode and transferring them to the light emitting layer, a material having high mobility for electrons is suitable. Specific examples include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited to these.
  • the thickness of the electron transport layer may be 1 to 50 nm.
  • the thickness of the electron transport layer is 1 nm or more, there is an advantage of preventing the electron transport properties from deteriorating, and when it is 50 nm or less, the thickness of the electron transport layer is too thick to prevent the driving voltage from rising to improve the movement of electrons. There is an advantage.
  • the electron injection layer may serve to facilitate injection of electrons.
  • the electron injection material has the ability to transport electrons, has an electron injection effect from the cathode, has an excellent electron injection effect for the light emitting layer or the light emitting material, prevents movement of excitons generated in the light emitting layer to the hole injection layer, and also , A compound having excellent thin film forming ability is preferred.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, fluorenylidene methane, anthrone and the like and their derivatives, metal Complex compounds, nitrogen-containing 5-membered ring derivatives, and the like, but are not limited thereto.
  • Examples of the metal complex compound include 8-hydroxyquinolinato lithium, bis(8-hydroxyquinolinato) zinc, bis(8-hydroxyquinolinato) copper, and bis(8-hydroxyquinolinato) manganese, Tris(8-hydroxyquinolinato)aluminum, tris(2-methyl-8-hydroxyquinolinato)aluminum, tris(8-hydroxyquinolinato)gallium, bis(10-hydroxybenzo[h] Quinolinato) beryllium, bis(10-hydroxybenzo[h]quinolinato) zinc, bis(2-methyl-8-quinolinato)chlorogallium, bis(2-methyl-8-quinolinato)( There are o-cresolato) gallium, bis (2-methyl-8-quinolinato) (1-naphtholato) aluminum, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, It is not limited to this.
  • the hole blocking layer is a layer that prevents the cathode from reaching the hole, and may be generally formed under the same conditions as the hole injection layer. Specifically, there are oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complex, and the like, but are not limited thereto.
  • the organic light emitting device may be a front emission type, a back emission type, or a double-sided emission type depending on the material used.
  • N,N'-((diphenylsilane)bis(5-(tert-butyl)-3,1-phenylene))bis(adamantan-1-amine) 50g, (3,4- Dibromo-5-iodophenyl) (difluoro(phenyl)methyl) sulfine 36g, sodium-tert-butoxide 19.7g and bis(tri-tert-butylphosphine)palladium(0) 0.4g toluene 600ml The mixture was stirred at reflux for 12 hours. After extraction after completion of the reaction, after purification with an ethyl acetate:hexane column, intermediate 18-1 (14.9g, yield 21%) was obtained through recrystallization. MS[M+H]+ 1054
  • a glass substrate coated with a thin film coated with ITO (indium tin oxide) at a thickness of 1,500 ⁇ was put 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 washing was repeated for 10 minutes by repeating it twice with distilled water.
  • ultrasonic cleaning was performed with a solvent of isopropyl alcohol, acetone, and methanol, followed by drying, and then transported to a plasma cleaner.
  • the substrate was washed for 5 minutes using oxygen plasma, and then transferred to a vacuum evaporator.
  • the following chemical formula [HAT] was thermally vacuum-deposited to a thickness of 50 Pa to form a hole injection layer.
  • the following formula [NPB] was vacuum-deposited to a thickness of 1100 MPa on the hole injection layer to form a hole transport layer.
  • the following formula [HT-A] was vacuum deposited on the hole transport layer to a thickness of 200 ⁇ to form an electron blocking layer.
  • the second electron transport layer aluminum was deposited to a thickness of 1,000 mm 2 to form a cathode.
  • the deposition rate of the organic material was maintained at 0.4 to 0.9 ⁇ /sec
  • the lithium fluoride of the second electron transport layer was 0.3 0.3/sec
  • the aluminum of the negative electrode was maintained at a deposition rate of 2 ⁇ /sec.
  • Vacuum degree is 5 ⁇ 10 -8 ⁇ 1 ⁇ 10 -7
  • the torr was maintained to produce an organic light emitting device.
  • An organic light emitting diode was manufactured according to the same method as Example 1 except for using the dopant compound shown in Table 1 below as a light emitting layer dopant material instead of the compound 1 of Example 1.
  • Example 1 Compound 1 8.7 3.7 185 Example 2 Compound 2 8.7 3.7 188 Example 3 Compound 3 8.6 3.8 186 Example 4 Compound 4 8.6 3.8 189 Example 5 Compound 5 8.2 3.7 178 Example 6 Compound 6 8.2 3.7 179 Example 7 Compound 7 8.7 3.6 185 Example 8 Compound 8 8.6 3.7 186 Example 9 Compound 9 8.4 3.7 183 Example 10 Compound 10 8.9 3.8 189 Example 11 Compound 11 8.6 3.7 180 Example 12 Compound 12 8.7 3.7 181 Example 13 Compound 13 8.6 3.7 182 Example 14 Compound 14 8.8 3.8 183 Example 15 Compound 15 8.7 3.8 183 Example 16 Compound 16 8.7 3.7 182 Example 17 Compound 17 8.7 3.8 182 Example 18 Compound 18 8.6 3.8 183 Comparative Example 1 Compound BD 7.1 4.1 163
  • the devices of Examples 1 to 18 using the compound having the structure of Formula 1 have lower voltage, higher efficiency, and higher lifespan characteristics than the devices of Comparative Example 1. This is due to the substitution of the electron acceptor material at the para position of boron, which increases the polarity of the material, which results in improved charge transfer characteristics, and at the same time, a material having a structurally tetrahedral structure. By being substituted, it seems that the orientation characteristics of the material increase and the efficiency increases. In addition, the electron injection characteristic is strong and the driving voltage is reduced. The lifespan also showed a more stable effect in terms of balance of electrons and holes, showing an increasing pattern.

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Abstract

La présente invention concerne un composé représenté par la formule chimique 1 et un élément électroluminescent organique le comprenant.
PCT/KR2019/018487 2018-12-26 2019-12-26 Composé et élément électroluminescent organique le comprenant WO2020138964A1 (fr)

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US20200392165A1 (en) * 2020-06-30 2020-12-17 Shanghai Tianma AM-OLED Co,Ltd. Compound, display panel and display apparatus

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