WO2017061832A1 - Nouveau composé et diode électroluminescente organique comprenant celui-ci - Google Patents

Nouveau composé et diode électroluminescente organique comprenant celui-ci Download PDF

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WO2017061832A1
WO2017061832A1 PCT/KR2016/011278 KR2016011278W WO2017061832A1 WO 2017061832 A1 WO2017061832 A1 WO 2017061832A1 KR 2016011278 W KR2016011278 W KR 2016011278W WO 2017061832 A1 WO2017061832 A1 WO 2017061832A1
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group
substituted
unsubstituted
compound
layer
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PCT/KR2016/011278
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English (en)
Korean (ko)
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하재승
홍완표
서상덕
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주식회사 엘지화학
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Priority claimed from KR1020160037179A external-priority patent/KR101781739B1/ko
Application filed by 주식회사 엘지화학 filed Critical 주식회사 엘지화학
Priority to EP16853948.4A priority Critical patent/EP3348552B1/fr
Priority to US15/765,740 priority patent/US10686138B2/en
Priority to CN201680058200.XA priority patent/CN108137527B/zh
Priority to JP2018515481A priority patent/JP6760581B2/ja
Publication of WO2017061832A1 publication Critical patent/WO2017061832A1/fr

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    • 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
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C211/00—Compounds containing amino groups bound to a carbon skeleton
    • C07C211/43—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton
    • C07C211/54—Compounds containing amino groups bound to a carbon skeleton having amino groups bound to carbon atoms of six-membered aromatic rings of the carbon skeleton having amino groups bound to two or three six-membered aromatic rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D311/00—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings
    • C07D311/02—Heterocyclic compounds containing six-membered rings having one oxygen atom as the only hetero atom, condensed with other rings ortho- or peri-condensed with carbocyclic rings or ring systems
    • C07D311/78—Ring systems having three or more relevant rings
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present specification relates to a novel compound and an organic light emitting device including the same.
  • 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 material layer is often made of a multi-layered structure composed of different materials to increase the efficiency and stability of the organic light emitting device, for example, it may be made of a hole injection layer, a hole transport layer, a light emitting layer, an electron transport layer, an electron injection layer.
  • the present invention seeks to provide a compound having a low driving voltage and a long service life.
  • the present invention is to provide an organic light emitting device comprising the compound.
  • An exemplary embodiment of the present specification may provide a compound represented by the following Formula 1.
  • R1 to R3 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Substituted or unsubstituted silyl group; Substituted or unsubstituted boron group; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryloxy group; Substituted or unsubstituted alkylthioxy group; Substituted or unsubstituted arylthioxy group; Substituted or unsubstituted alkyl sulfoxy group; Substituted or unsubstituted aryl sulfoxy group; Substituted or unsubstituted alkenyl group; A substitute
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; It is any one selected from the group consisting of a substituted or unsubstituted fluorene group and a substituted or unsubstituted heterocyclic group,
  • Ar1 and Ar2 may be bonded to each other with an adjacent group to form a substituted or unsubstituted ring,
  • n and m are each an integer of 0 to 6
  • o + s is an integer from 1 to 4,
  • s, p and q are integers from 1 to 4.
  • an exemplary embodiment of the present specification 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 the compound of Formula 1. have.
  • the compound according to the exemplary embodiment of the present specification is used as a material of the organic material layer of the organic light emitting device, and may bring about an effect of improving efficiency of the organic light emitting device, low driving voltage and lifespan characteristics.
  • the compound according to one embodiment of the present specification may be used as a hole injection, hole transport, electron transport and electron injection or a light emitting material.
  • An exemplary embodiment of the present specification provides a compound represented by Chemical Formula 1.
  • the term "substituted or unsubstituted” is deuterium; Halogen group; Nitrile group; Nitro group; Hydroxyl group; Carbonyl group; Ester group; Imide group; Amino group; Phosphine oxide groups; An alkoxy group; Aryloxy group; Alkyl thioxy group; Arylthioxy group; Alkyl sulfoxy groups; Aryl sulfoxy group; Silyl groups; Boron group; Alkyl groups; Cycloalkyl group; Alkenyl groups; Aryl group; Aralkyl group; Ar alkenyl group; Alkylamine group; Aralkyl amine groups; Arylamine group; And it is substituted or unsubstituted with one or more substituents selected from the group consisting of an aryl phosphine group, or substituted or unsubstituted two or more substituents of the substituents exemplified above.
  • 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.
  • adjacent means a substituent substituted on an atom directly connected to an atom to which the substituent is substituted, a substituent positioned closest to the substituent, or another substituent substituted on an atom to 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.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • 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 25 carbon atoms or an aryl group having 6 to 25 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 includes trimethylsilyl group, triethylsilyl group, t-butyldimethylsilyl group, vinyldimethylsilyl group, propyldimethylsilyl group, triphenylsilyl group, diphenylsilyl group, phenylsilyl group, and the like.
  • the present invention is not limited thereto.
  • the boron group specifically includes, but is not limited to, trimethylboron group, triethylboron group, t-butyldimethylboron group, triphenylboron group, 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 40. According to an 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. According to another exemplary embodiment, the alkyl group has 1 to 6 carbon atoms.
  • alkyl group examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec-butyl, 1-methyl-butyl, 1-ethyl-butyl, pentyl, n -Pentyl, isopentyl, neopentyl, tert-pentyl, hexyl, n-hexyl, 1-methylpentyl, 2-methylpentyl, 4-methyl-2-pentyl, 3,3-dimethylbutyl, 2-ethylbutyl, heptyl , n-heptyl, 1-methylhexyl, cyclopentylmethyl, cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl
  • the alkenyl group may be linear or branched chain, the carbon number is not particularly limited, but is preferably 2 to 40. According to an exemplary embodiment, the alkenyl group has 2 to 20 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 10 carbon atoms. According to another exemplary embodiment, the alkenyl group has 2 to 6 carbon atoms.
  • 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, stilbenyl group, styrenyl 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.
  • examples of the arylamine group include substituted or unsubstituted monocyclic diarylamine groups, substituted or unsubstituted polycyclic diarylamine groups or substituted or unsubstituted monocyclic and polycyclic diaryls. It means an amine group.
  • 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 a monocyclic aryl group, but may be a phenyl group, a biphenyl group, a terphenyl group, etc., but is not limited thereto.
  • the polycyclic aryl group may be naphthyl group, anthracenyl group, phenanthryl group, pyrenyl group, perylenyl group, chrysenyl group, fluorenyl group, and the like, but is not limited thereto.
  • the fluorenyl group may be substituted, and two substituents may be bonded to each other to form a spiro structure.
  • the heterocyclic group is a heterocyclic group containing one or more of N, O, S, Si, and Se as hetero atoms, and the carbon number is not particularly limited, but is preferably 2 to 60 carbon atoms.
  • the heterocyclic group include thiophene group, furan group, pyrrole group, imidazole group, thiazole group, oxazole group, oxadiazole group, triazole group, pyridyl group, bipyridyl group, pyrimidyl group, triazine group, triazole group, Acridyl group, pyridazine group, pyrazinyl group, quinolinyl group, quinazoline group, quinoxalinyl group, phthalazinyl group, pyrido pyrimidinyl group, pyrido pyrazinyl group, pyrazino pyrazinyl group, isoquinoline group , Indole group, carb
  • heterocycle is a divalent group.
  • heterocyclic group may be applied except that the heteroaryl group is aromatic.
  • the aryloxy group, the arylthioxy group, the aryl sulfoxy group, the aryl phosphine group, the aralkyl group, the aralkylamine group, the aryl group in the aralkenyl group, the arylamine group, the description of the above-described aryl group can be applied.
  • an alkyl thioxy group, an alkyl sulfoxy group, an aralkyl group, an aralkyl amine group, and an alkyl group among the alkyl amine groups may be described with respect to the aforementioned alkyl group.
  • heteroaryl group the heteroaryl group of the heteroarylamine group, the description of the aforementioned heterocyclic group may be applied.
  • alkenyl group of the alkenyl group may be applied to the description of the alkenyl group described above.
  • heteroarylene is a divalent group.
  • the meaning of combining with adjacent groups to form a ring means combining with adjacent groups with each other for a substituted or unsubstituted aliphatic hydrocarbon ring; Substituted or unsubstituted aromatic hydrocarbon ring; Substituted or unsubstituted aliphatic heterocycle; Or to form a substituted or unsubstituted aromatic heterocycle.
  • the aliphatic hydrocarbon ring means a ring composed only of carbon and hydrogen atoms as a ring which is not aromatic.
  • examples of the aromatic hydrocarbon ring include, but are not limited to, phenyl group, naphthyl group, anthracenyl group, and the like.
  • the aliphatic heterocycle means an aliphatic ring containing one or more of the heteroatoms.
  • the aromatic heterocycle means an aromatic ring including at least one of heteroatoms.
  • the aliphatic hydrocarbon ring, aromatic hydrocarbon ring, aliphatic hetero ring and aromatic hetero ring may be monocyclic or polycyclic.
  • R1 to R3 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted cycloalkyl group; Substituted or unsubstituted alkenyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted aralkenyl group; Substituted or unsubstituted alkylaryl group; A substituted or unsubstituted aralkylamine group; Substituted or unsubstituted arylamine group; Substituted or unsubstituted aryl group; And it is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group.
  • R1 to R3 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted alkyl group; A substituted or unsubstituted aralkyl group; Substituted or unsubstituted alkylaryl group; Substituted or unsubstituted aryl group; And it is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group.
  • R1 to R3 are each independently hydrogen; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; And it is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group.
  • R1 to R3 are each independently hydrogen; Alkyl groups; Aryl group; And heterocyclic group is any one selected from the group consisting of.
  • L1 to L3 is a direct bond; Or a divalent linking group.
  • L1 to L3 is a direct bond; Substituted or unsubstituted alkylene group; A substituted or unsubstituted cycloalkylene group; Substituted or unsubstituted alkenylene group; Substituted or unsubstituted aralkylene group; A substituted or unsubstituted aralkenylene group; Substituted or unsubstituted alkyl arylene group; A substituted or unsubstituted divalent amine group; Substituted or unsubstituted divalent aralkyl amine group; Substituted or unsubstituted divalent arylamine group; Substituted or unsubstituted arylene group; And it is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group.
  • L1 to L3 is a direct bond; Substituted or unsubstituted alkylene group; Substituted or unsubstituted aralkylene group; A substituted or unsubstituted aralkenylene group; Substituted or unsubstituted alkyl arylene group; A substituted or unsubstituted divalent amine group; Substituted or unsubstituted divalent aralkyl amine group; Substituted or unsubstituted divalent arylamine group; Substituted or unsubstituted arylene group; And it is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group.
  • L1 to L3 is a direct bond; A substituted or unsubstituted divalent amine group; Substituted or unsubstituted divalent arylamine group; Substituted or unsubstituted arylene group; And it is any one selected from the group consisting of a substituted or unsubstituted heterocyclic group.
  • L1 to L3 is a direct bond; Divalent amine groups substituted with aryl groups; Divalent arylamine group; An arylene group substituted with an amine group or an alkyl group; And heterocyclic group is any one selected from the group consisting of.
  • L1 to L3 is any one of the following formula.
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Halogen group; Nitrile group; Nitro group; Substituted or unsubstituted amine group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted alkoxy group; Substituted or unsubstituted aryl group; It is any one selected from the group consisting of a substituted or unsubstituted fluorene group and a substituted or unsubstituted heteroring group.
  • Ar1 and Ar2 are each independently hydrogen; heavy hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; It is any one selected from the group consisting of a substituted or unsubstituted fluorene group and a substituted or unsubstituted heteroring group.
  • Ar1 and Ar2 are each independently hydrogen; Substituted or unsubstituted amine group; Substituted or unsubstituted aryl group; It is any one selected from the group consisting of a substituted or unsubstituted fluorene group and a substituted or unsubstituted heteroring group.
  • Ar1 and Ar2 are each independently hydrogen; Amine groups substituted with aryl groups; Aryl group; It is any one selected from the group consisting of a fluorene group substituted with an aryl group and a heterocyclic group substituted with an aryl group.
  • L1 to L3, Ar1 and Ar2 may be combined with an adjacent group to form a substituted or unsubstituted ring.
  • Ar1 and Ar2 may combine with each other to form a substituted or unsubstituted ring.
  • the substituted or unsubstituted ring formed by combining Ar1 and Ar2 with each other is any one of the following formulae.
  • R4 to R9 are each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted fluorene group; And it is selected from the group consisting of a substituted or unsubstituted heterocyclic group.
  • a is an integer from 1 to 10
  • b to e are integers of 1 to 8, respectively.
  • R4 to R9 are each independently a substituted or unsubstituted alkyl group; And it is selected from the group consisting of a substituted or unsubstituted aryl group.
  • R4 to R9 are each independently an alkyl group; And an aryl group.
  • L1 to L3 and Ar1 or Ar2 may be bonded to each other to form a substituted or unsubstituted ring.
  • the substituted or unsubstituted ring formed by combining L1 to L3 and Ar1 or Ar2 with each other is any one of the following formulae.
  • R10 to R15 are each independently a substituted or unsubstituted alkyl group; Substituted or unsubstituted aryl group; Substituted or unsubstituted fluorene group; And it is selected from the group consisting of a substituted or unsubstituted heterocyclic group,
  • Ar3 is Ar1 or Ar2,
  • f is an integer from 1 to 9
  • g to j are each an integer of 1-7.
  • R10 to R15 are each independently a substituted or unsubstituted alkyl group; And it is selected from the group consisting of a substituted or unsubstituted aryl group.
  • R10 to R15 are each independently an alkyl group; And an aryl group.
  • n and m in the general formula 1 are each an integer of 0 to 6
  • o + s is an integer of 1 to 4
  • s is an integer of 1 to 4.
  • R1 When n or m is 0, there is no substituent of R1 or R2, and it means that only hydrogen is substituted.
  • R3 and L1 may be substituted in the lower right benzene ring of the core structure, and the number of substituents thereof may not exceed four.
  • L1 means that at least one is substituted, and when s is 4 means that L1 is substituted at all positions where the substituent may be located, and R3 is not present.
  • the compound of the present invention is any one of the following formula.
  • an organic light emitting device including one or more organic material layers provided between the first electrode and the second electrode, wherein at least one of the organic material layer comprises a compound of Formula 1
  • An organic light emitting element can be provided.
  • the organic material layer of the organic light emitting device of the present specification may be formed of a single layer structure, but may be formed of a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device of the present invention may have a structure including a hole generating layer, a hole transport layer, a hole buffer layer, a light emitting layer and the like as an organic material layer.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic material layer includes a hole generating layer, a hole transporting layer, a hole buffer layer or a layer for simultaneously generating and transporting the hole, and the hole generating layer, the hole transporting layer, the hole buffer layer, or the hole generating and transporting.
  • the layer may include the compound of formula (1).
  • the organic material layer may include a light emitting layer, and the light emitting layer may include the compound of Formula 1.
  • the organic light emitting diode may be an organic light emitting diode having a structure in which an anode, one or more organic material layers, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting diode may be an organic light emitting diode having an inverted type in which a cathode, one or more organic material layers, and an anode are sequentially stacked on a substrate.
  • the organic light emitting device of the present specification may have a laminated structure as follows, but is not particularly limited thereto.
  • the first electrode is an electrode for injecting holes
  • the material of the first electrode may be a material having a large work function to facilitate hole injection into the 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), indium zinc oxide (IZO); ZnO: Al or SNO 2 : Combination of metals and oxides such as 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 hole injection layer may play a role of smoothly injecting holes from the first electrode to the light emitting layer.
  • the hole injection layer may include the compound of Formula 1.
  • the hole injection layer may be made of only the compound of Formula 1, but the compound of Formula 1 may be present in a mixed or doped state to another hole injection layer material known in the art.
  • the compound of Formula 1 may account for 100% of the hole injection layer, but may be doped with 0.1 to 50% by weight.
  • the compound of Formula 1 is a derivative having an indenofluorene structure, has excellent electron acceptability, and may improve power consumption and lower driving voltage.
  • 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 that the hole injection characteristics can be prevented from being lowered.
  • the thickness of the hole injection layer is 150 nm or less, the thickness of the hole injection layer is so thick that the driving voltage is increased to improve the movement of holes. There is an advantage that can be prevented from being raised.
  • the hole injection layer material hole injection materials known in the art may be used.
  • hole injection layer material CuPc (cupper phthalocyanine), PEDOT (poly (3,4) -ethylenedioxythiophene), PANI (polyaniline) and NPD (N, N-dinaphthyl-N, N'-diphenyl benzidine) Any one or more selected may be used, but is not limited thereto.
  • the hole transport layer may serve to facilitate the transport of holes.
  • the hole transport layer may include the compound of Formula 1.
  • the hole transport layer may be made of only the compound of Formula 1, but the compound of Formula 1 may be present in a mixed or doped state with other hole transport layer materials known in the art.
  • the compound of Formula 1 may account for 100% of the hole transport layer, but may be doped with 0.1 to 50% by weight.
  • Other hole transport material may be a hole transport material known in the art.
  • the hole transport layer may be NPD (N, N-dinaphthyl-N, N'-diphenylbenzidine), TPD (N, N'-bis- (3-methylphenyl) -N, N'-bis- (phenyl) -benzidine), s-TAD and MTDATA (4,4 ', 4 "-Tris (N-3-methylphenyl-N-phenyl-amino) -triphenylamine), but may be composed of one or more selected from the group consisting of, but not limited thereto.
  • triazole derivatives As the hole transport layer material, triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkaine derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino substituted chalcone derivatives, oxazole derivatives, Styryl anthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, polysilane-based, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers) and the like.
  • a hole buffer layer may be further provided between the hole injection layer and the hole transport layer.
  • the hole buffer layer may include the compound of Formula 1, and may include other hole injection or transport materials known in the art. Even when the hole buffer layer includes the compound of Chemical Formula 1, the hole buffer layer may be made of only the compound of Chemical Formula 1, but may be formed in a mixture or doped state of the compound of Chemical Formula 1 with another host material.
  • An electron suppression layer may be provided between the hole transport layer and the light emitting layer, and the compound of Formula 1 or a material known in the art may be used.
  • the light emitting layer may emit red, green, and / or blue, and may be formed of a phosphor or a fluorescent material.
  • the light emitting layer material can use those known in the art.
  • Carbazole biphenyl (CBP) or mCP (1,3-bis (carbazol-9-yl)) may be used as the light emitting host material, but is not limited thereto.
  • light emitting dopants include PIQIr (acac) (bis (1-phenylisoquinoline) acetylacetonate iridium), PQIr (acac) (bis (1-phenylquinoline) acetylacetonate iridium) and PQIr (tris (1-phenylquinoline) phosphorescent materials such as iridium), octaethylporphyrin platinum (PtOEP), or fluorescent materials such as tris (8-hydroxyquinolino) aluminum (Alq3) may be used, but the present invention is not limited thereto.
  • a phosphor such as Ir (ppy) 3 (fac tris (2-phenylpyridine) iridium) or a fluorescent material such as Alq3 (tris (8-hydroxyquinolino) aluminum
  • 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.
  • a hole suppression layer may be provided between the electron transport layer and the light emitting layer, and a material known in the art may be used.
  • the electron transport layer may serve to facilitate the transport of electrons.
  • Materials known in the art can be used, such as Alq3 (tris (8-hydroxyquinolino) aluminum), PBD, TAZ, spiro-PBD, BAlq, SAlq.
  • the electron transport layer may have a thickness of about 1 nm to about 50 nm. In this case, when the thickness of the electron transport layer is 1 nm or more, there is an advantage that the electron transporting property may be prevented from being lowered. When the thickness of the electron transport layer is 50 nm or less, the thickness of the electron transport layer is too thick, and the driving voltage is increased to improve the movement of electrons. There is an advantage that can be prevented.
  • the electron injection layer may play a role of smoothly injecting electrons.
  • Alq3 tris (8-hydroxyquinolino) aluminum
  • PBD tris (8-hydroxyquinolino) aluminum
  • TAZ spiro-PBD
  • BAlq or SAlq can be made of organic materials, complexes or metal compounds known in the art.
  • Metal compounds include metal halides, and storage can be used, for example, can be used LiQ, LiF, NaF, KF, RbF, CsF, FrF, BeF 2, MgF 2, CaF 2, SrF 2, BaF 2 and RaF 2 and the like.
  • the electron injection layer may have a thickness of about 1 nm to about 50 nm.
  • the thickness of the electron injection layer is 1 nm or more, there is an advantage that the electron injection characteristics can be prevented from being lowered.
  • the thickness of the electron injection layer is 50 nm or less, the thickness of the electron injection layer is so thick that the driving voltage is increased to improve the movement of electrons. There is an advantage that can be prevented from being raised.
  • the second electrode may be a material having a small work function so as to easily inject electrons into the organic material layer as the electron injection electrode.
  • 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 organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound of the present specification, that is, the compound of Formula 1.
  • the organic material layers may be formed of the same material or different materials.
  • the organic light emitting device of the present specification may be manufactured by materials and methods known in the art, except that at least one layer of the organic material layer includes the compound represented by Chemical Formula 1, that is, the compound represented by Chemical Formula 1.
  • the organic light emitting device of the present specification may be manufactured by sequentially stacking a first electrode, an organic material layer, and a second electrode on a substrate.
  • a physical vapor deposition (PVD) method such as sputtering or e-beam evaporation
  • a metal or conductive metal oxide or an alloy thereof is deposited on the substrate to form an anode.
  • an organic material layer including a hole injection layer, a hole transport layer, a light emitting layer, and an electron transport layer thereon, and then depositing a material that can be used as a cathode thereon.
  • 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 compound of Formula 1 may be formed of 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, doctor blading, inkjet printing, screen printing, spray method, roll coating, etc., but is not limited thereto.
  • an organic light emitting device may be manufactured by sequentially depositing an organic material layer and an anode material on a substrate from a cathode material.
  • International Patent Application Publication No. 2003/012890 International Patent Application Publication No. 2003/012890.
  • the manufacturing method is not limited thereto.
  • the first electrode may be an anode
  • the second electrode may be a cathode
  • the first electrode may be a cathode
  • the second electrode may be an anode
  • the hole injection material is a layer for injecting holes from an electrode, and the hole injection material has a capability of transporting holes, and thus has a hole injection effect at an anode, an excellent hole injection effect for a light emitting layer or a light emitting material, and is generated in a light emitting layer.
  • the compound which prevents the movement of the excited excitons to the electron injection layer or the electron injection material, and is excellent in thin film formation ability is preferable.
  • hole injection material examples include metal porphyrin, oligothiophene, arylamine-based organic material, hexanitrile hexaazatriphenylene-based organic material, quinacridone-based organic material, and perylene-based Organic materials, anthraquinone, and polyaniline and polythiophene-based conductive polymers, but are not limited thereto.
  • the hole transport layer is a layer that receives holes from the hole injection layer and transports holes to the light emitting layer.
  • the hole transport material is a material capable of transporting holes from the anode or the hole injection layer to the light emitting layer.
  • the material 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.
  • 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.
  • the light emitting layer may include a host material and a dopant material.
  • the host material is a condensed aromatic ring derivative or a heterocyclic containing compound.
  • 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.
  • Dopant materials include aromatic amine derivatives, styrylamine compounds, boron complexes, fluoranthene compounds, metal complexes, and the like.
  • the aromatic amine derivatives include condensed aromatic ring derivatives having a substituted or unsubstituted arylamino group, and include pyrene, anthracene, chrysene, and periplanthene having an arylamino group, and a styrylamine compound may be substituted or unsubstituted.
  • At least one arylvinyl group is substituted with the substituted arylamine, and one or two or more substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • substituents selected from the group consisting of an aryl group, a silyl group, an alkyl group, a cycloalkyl group and an arylamino group are substituted or unsubstituted.
  • the metal complex includes, but is not limited to, an iridium complex, a platinum complex, and the like.
  • the electron transporting material is a layer that receives electrons from the electron injection layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material that can inject electrons well from the cathode and move them to the light emitting layer. This is suitable. Specific examples thereof include Al complexes of 8-hydroxyquinoline; Complexes including Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes and the like, but are not limited thereto.
  • the electron transport layer can be used with any desired cathode material as used in accordance with the prior art.
  • suitable cathode materials are conventional materials having a low work function followed by an aluminum or silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, followed by aluminum layers or silver layers in each case.
  • the electron injection layer is a layer that injects electrons from an electrode, has an ability of transporting electrons, has an electron injection effect from a cathode, an electron injection effect with respect to a light emitting layer or a light emitting material, and hole injection of excitons generated in the light emitting layer.
  • the compound which prevents the movement to a layer and is excellent in thin film formation ability is preferable.
  • fluorenone anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, anthrone and the like and derivatives thereof, metal Complex compounds, 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 organic light emitting device may be a top emission type, a bottom emission type, or a double side emission type according to a material used.
  • Compound A2 was prepared by the same method as in the synthesis of A1, except that 3-bromofluorene was used instead of compound 2-bromofluorene.
  • Compound A3 was prepared by the same method as in the synthesis of A1, except that 4-bromofluorene was used instead of compound 2-bromofluorene.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • Hexanitrile hexaazatriphenylene was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • Compound 1 (300 Pa) synthesized in Preparation Example 1-1 which is a material for transporting holes thereon, was vacuum deposited, and then HT 2 was vacuum deposited to a film thickness of 100 Pa on the hole transport layer to form a hole control layer.
  • the host H1 and the dopant D1 compound (25: 1) were vacuum deposited to a thickness of 300 kPa.
  • E1 compound (300 kPa) was thermally vacuum deposited sequentially into the electron injection and transport layer.
  • An organic light emitting device was manufactured by sequentially depositing 12 ⁇ thick lithium fluoride (LiF) and 2,000 ⁇ thick aluminum on the electron transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the lithium fluoride was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
  • Table 1 shows the results of experimenting with the organic light emitting device manufactured by using each compound as the hole transporting material as in Examples 1 to 5 and Comparative Example 1.
  • Example 1 As shown in Table 1, the compounds used in Examples 1 to 5 were used as the hole transport layer in the organic light emitting device, and it can be seen that they exhibit lower voltage and higher efficiency than Comparative Example 1, which is a benzidine type material.
  • a glass substrate (corning 7059 glass) coated with ITO (Indium Tin Oxide) with a thickness of 1,000 ⁇ was placed in distilled water in which a dispersant was dissolved, and ultrasonically washed. Fischer Co. products were used for the detergent, and Millipore Co. Secondly filtered distilled water was used as a filter of the product. After the ITO was washed for 30 minutes, the ultrasonic cleaning was repeated twice with distilled water for 10 minutes. After washing the distilled water, the ultrasonic washing in the order of isopropyl alcohol, acetone, methanol solvent and dried.
  • ITO Indium Tin Oxide
  • the hexanitrile hexaazatriphenylene (hexanitrile hexaazatriphenylene) mentioned above was thermally vacuum deposited to a thickness of 500 kPa on the prepared ITO transparent electrode to form a hole injection layer.
  • HT1 (300 Pa) synthesized in Preparation Example 2-1 which is a material for transporting holes, was vacuum-deposited, followed by vacuum deposition of Compound 6 at a film thickness of 100 Pa on the hole transport layer to form a hole control layer.
  • the host H1 and the dopant D1 compound (25: 1) were vacuum deposited to a thickness of 300 kPa.
  • E1 compound 300 kPa was thermally vacuum deposited sequentially into the electron injection and transport layer.
  • An organic light emitting device was manufactured by sequentially depositing 12 ⁇ thick lithium fluoride (LiF) and 2,000 ⁇ thick aluminum on the electron transport layer to form a cathode.
  • the deposition rate of the organic material was maintained at 1 ⁇ / sec
  • the lithium fluoride was 0.2 ⁇ / sec
  • the aluminum was maintained at a deposition rate of 3 to 7 ⁇ / sec.
  • the compound derivative of the formula according to the present invention may play a role of hole transport and hole control in organic electronic devices, including organic light emitting devices, the device according to the present invention exhibits excellent characteristics in terms of efficiency, driving voltage, stability.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne un composé représenté par la formule chimique 1, et une diode électroluminescente organique le comprenant.
PCT/KR2016/011278 2015-10-07 2016-10-07 Nouveau composé et diode électroluminescente organique comprenant celui-ci WO2017061832A1 (fr)

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EP16853948.4A EP3348552B1 (fr) 2015-10-07 2016-10-07 Derives de 2,7-di(naphthalen-1-yl)spiro[fluorene-9,9'-xanthene pour utilisation dans diodes electroluminescente
US15/765,740 US10686138B2 (en) 2015-10-07 2016-10-07 Compound and organic light emitting diode comprising same
CN201680058200.XA CN108137527B (zh) 2015-10-07 2016-10-07 新化合物和包含其的有机发光二极管
JP2018515481A JP6760581B2 (ja) 2015-10-07 2016-10-07 新規化合物およびこれを含む有機発光素子

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KR1020160037179A KR101781739B1 (ko) 2015-10-07 2016-03-28 신규 화합물 및 이를 포함하는 유기 발광 소자

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JP2020516068A (ja) * 2017-05-29 2020-05-28 エルジー・ケム・リミテッド 有機発光素子
KR20190015211A (ko) 2017-08-03 2019-02-13 이데미쓰 고산 가부시키가이샤 화합물, 유기 전기발광 소자용 재료, 유기 전기발광 소자, 및 전자 기기
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WO2019027040A1 (fr) 2017-08-03 2019-02-07 出光興産株式会社 Composé, matériau d'élément électroluminescent organique, élément électroluminescent organique et dispositif électronique
JPWO2019027040A1 (ja) * 2017-08-03 2020-08-20 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器
JP7033140B2 (ja) 2017-08-03 2022-03-09 出光興産株式会社 化合物、有機エレクトロルミネッセンス素子用材料、有機エレクトロルミネッセンス素子、及び電子機器
KR102125619B1 (ko) * 2017-10-20 2020-06-22 주식회사 엘지화학 신규 화합물 및 이를 포함하는 유기 발광 소자
KR20190044577A (ko) * 2017-10-20 2019-04-30 주식회사 엘지화학 신규 화합물 및 이를 포함하는 유기 발광 소자
CN111051291A (zh) * 2017-10-20 2020-04-21 株式会社Lg化学 新型化合物及包含其的有机发光器件
CN109694378A (zh) * 2017-10-22 2019-04-30 机光科技股份有限公司 多杂芳族化合物及使用其的有机电激发光元件
CN111201624A (zh) * 2018-01-11 2020-05-26 株式会社Lg化学 有机发光二极管
CN111201624B (zh) * 2018-01-11 2023-09-12 株式会社Lg化学 有机发光二极管
CN111213251A (zh) * 2018-02-28 2020-05-29 株式会社Lg化学 有机发光二极管
CN111201623B (zh) * 2018-02-28 2023-11-10 株式会社Lg化学 有机发光二极管
CN111201623A (zh) * 2018-02-28 2020-05-26 株式会社Lg化学 有机发光二极管
CN111213251B (zh) * 2018-02-28 2023-09-29 株式会社Lg化学 有机发光二极管
CN110818670A (zh) * 2018-08-07 2020-02-21 乐金显示有限公司 化合物和有机发光装置
CN110818670B (zh) * 2018-08-07 2023-08-08 乐金显示有限公司 化合物和有机发光装置
WO2020159019A1 (fr) * 2019-01-30 2020-08-06 두산솔루스 주식회사 Composé électroluminescent organique, et dispositif électroluminescent organique l'utilisant
US11917909B2 (en) 2019-01-30 2024-02-27 Solus Advanced Materials Co., Ltd. Organic compound and organic electroluminescence device using the same
WO2020218680A1 (fr) * 2019-04-25 2020-10-29 두산솔루스 주식회사 Composé organique et diode électroluminescente organique l'utilisant
KR102199111B1 (ko) 2020-02-17 2021-01-06 솔루스첨단소재 주식회사 유기 화합물 및 이를 이용한 유기 전계 발광 소자
KR20200125417A (ko) * 2020-02-17 2020-11-04 두산솔루스 주식회사 유기 화합물 및 이를 이용한 유기 전계 발광 소자

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