WO2019147077A1 - Composé et dispositif électroluminescent organique le comprenant - Google Patents

Composé et dispositif électroluminescent organique le comprenant Download PDF

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WO2019147077A1
WO2019147077A1 PCT/KR2019/001116 KR2019001116W WO2019147077A1 WO 2019147077 A1 WO2019147077 A1 WO 2019147077A1 KR 2019001116 W KR2019001116 W KR 2019001116W WO 2019147077 A1 WO2019147077 A1 WO 2019147077A1
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group
substituted
unsubstituted
compound
layer
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PCT/KR2019/001116
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English (en)
Korean (ko)
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차용범
홍성길
김성소
천민승
서상덕
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주식회사 엘지화학
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Priority to CN201980005366.9A priority Critical patent/CN111278803B/zh
Publication of WO2019147077A1 publication Critical patent/WO2019147077A1/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
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/633—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising polycyclic condensed aromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/14—Carrier transporting layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • 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
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1014—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/18—Carrier blocking layers
    • H10K50/181—Electron blocking layers

Definitions

  • the present invention relates to a compound and an organic light emitting device including the same.
  • the organic light emitting device has a structure in which an organic thin film is disposed between two electrodes. When a voltage is applied to the organic light emitting device having such a structure, electrons and holes injected from the two electrodes couple to each other in the organic thin film and form a pair, which then extinguishes and emits light.
  • the organic thin film may be composed of a single layer or a multilayer, if necessary.
  • the material of the organic thin film may have a light emitting function as needed.
  • a compound capable of forming a light emitting layer by itself may be used, or a compound capable of serving as a host or a dopant of a host-dopant light emitting layer may be used.
  • a compound capable of performing a role such as hole injection, hole transport, electron blocking, hole blocking, electron transport or electron injection may be used.
  • the present invention provides a compound and an organic light emitting device comprising the same.
  • An embodiment of the present invention provides a compound represented by the following formula (1).
  • R1 and R2 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or may be bonded to each other to form a substituted or unsubstituted ring,
  • L1 and L2 are the same or different from each other and are each independently a direct bond; Or a substituted or unsubstituted arylene group,
  • Ar 1 to Ar 3 are the same or different and each independently represents a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group.
  • the present application also includes a first electrode; A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound described above.
  • the compound according to one embodiment of the present application is used in an organic light emitting device to lower the driving voltage of the organic light emitting device, improve the light efficiency, and improve the lifetime characteristics of the device by the thermal stability of the compound.
  • the amine group was easily synthesized at the 2-position.
  • the compound according to one embodiment of the present application has an amine group at the 3-position of the fluorene core through a novel synthesis method, And a substituent is bonded to the second reactive site which is further reactive.
  • Such compounds of the present invention have an increased stability, a longer lifetime of the device, and a distorted molecular structure due to steric hindrance, thereby increasing the efficiency of the device.
  • FIG. 1 shows an example of an organic light emitting device in which a substrate 1, an anode 2, an organic material layer 3, and a cathode 4 are sequentially laminated.
  • Fig. 2 is a cross-sectional view showing a structure of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron restraining layer 7, a light emitting layer 8, a hole blocking layer 9, 10 and a cathode 4 are sequentially laminated on a substrate 1.
  • the present invention provides a compound represented by the above formula (1).
  • the compounds of the present invention are synthesized by a novel synthesis method, in which an aryl group or a heterocyclic group is bonded to the 2-position of the fluorene core and the amine structure is bonded to the 3-position of the fluorene core, Improves efficiency.
  • substituted means that the hydrogen atom bonded to the carbon atom of the compound is replaced with another substituent, and the substituted position is not limited as long as the substituent is a substitutable position, , Two or more substituents may be the same as or different from each other.
  • the term " substituted or unsubstituted" A halogen group; A nitrile group; A nitro group; An alkyl group; A cycloalkyl group; Silyl group; An amine group; An aryl group; And a heterocyclic group, or that at least two of the substituents exemplified in the above exemplified substituents are substituted with a connected substituent, or have no substituent.
  • a substituent to which at least two substituents are connected may be a biphenyl group. That is, the biphenyl group may be an aryl group, and may be interpreted as a substituent in which two phenyl groups are connected.
  • examples of the halogen group include fluorine, chlorine, bromine or iodine.
  • the alkyl group may be linear or branched, and the number of carbon atoms is not particularly limited, but is preferably 1 to 50.
  • Specific examples include methyl, ethyl, propyl, n-propyl, isopropyl, butyl, n-butyl, isobutyl, tert-butyl, sec- N-pentyl, 3-dimethylbutyl, 2-ethylbutyl, heptyl, n-hexyl, Cyclohexylmethyl, octyl, n-octyl, tert-octyl, 1-methylheptyl, 2-ethylhexyl, 2-propylpentyl, n-nonyl, 2,2-dimethyl Heptyl, 1-ethylpropyl, 1,1-dimethylpropyl, isohexyl, 2-methylpentyl, 4-methylhexyl, 5-methylhexyl
  • the cycloalkyl group is not particularly limited, but is preferably a group having 3 to 30 carbon atoms. Specific examples thereof include cyclopropyl, cyclobutyl, cyclopentyl, 3-methylcyclopentyl, 2,3-dimethylcyclopentyl, But are not limited to, methyl, ethyl, propyl, isopropyl, butyl, isobutyl, sec-butyl, isobutyl, sec-butyl, It is not.
  • the silyl group specifically includes a trimethylsilyl group, a triethylsilyl group, a t-butyldimethylsilyl group, a vinyldimethylsilyl group, a propyldimethylsilyl group, a triphenylsilyl group, a diphenylsilyl group,
  • the present invention is not limited thereto.
  • the amine group is -NH 2 ; Monoalkylamine groups; A dialkylamine group; N-alkylarylamine groups; Monoarylamine groups; A diarylamine group; An N-arylheteroarylamine group; An N-alkylheteroarylamine group, a monoheteroarylamine group, and a diheteroarylamine group.
  • the number of carbon atoms is not particularly limited, but is preferably 1 to 30.
  • amine group examples include methylamine, dimethylamine, ethylamine, diethylamine, phenylamine, naphthylamine, biphenylamine, anthracenylamine, 9-methyl- , Diphenylamine group, ditolylamine group, N-phenyltolylamine group, triphenylamine group, N-phenylbiphenylamine group; N-phenylnaphthylamine group; An N-biphenylnaphthylamine group; N-naphthylfluorenylamine group; N-phenylphenanthrenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-biphenyl phenanthrenyl amine group; N-phenylfluorenylamine group; An N-phenyltriphenylamine group; N-phenanthrenyl fluorenyl
  • the aryl group is a monocyclic aryl group
  • the number of carbon atoms is not particularly limited, but is preferably 6 to 30 carbon atoms.
  • Specific examples of the monocyclic aryl group include a phenyl group, a biphenyl group, a terphenyl group, and the like, but are not limited thereto.
  • the aryl group is a polycyclic aryl group
  • the number of carbon atoms is not particularly limited. And preferably has 10 to 24 carbon atoms.
  • Specific examples of the polycyclic aryl group include, but are not limited to, a naphthyl group, an anthracene group, a phenanthrene group, a pyrenyl group, a perylenyl group, a chrysene group and a fluorene group.
  • the heterocyclic group includes at least one non-carbon atom and at least one hetero atom.
  • the hetero atom may include at least one atom selected from the group consisting of O, N, Se, Si and S have.
  • the number of carbon atoms of the heterocyclic group is not particularly limited, but is preferably 2 to 60 carbon atoms or 2 to 30 carbon atoms.
  • heterocyclic group examples include a thiophene group, a furan group, a pyrrolyl group, an imidazolyl group, a thiazolyl group, an oxazolyl group, an oxadiazolyl group, a triazolyl group, a pyridyl group, a bipyridyl group, A pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, a pyrimidinyl group, , An isoquinolinyl group, an indole group, a
  • an arylene group means a divalent group having two bonding positions in an aryl group.
  • the description of the aryl group described above can be applied except that each of these is 2 groups.
  • adjacent means that the substituent is a substituent substituted on an atom directly connected to the substituted atom, a substituent stereostructically closest to the substituent, or another substituent substituted on the substituted atom .
  • two substituents substituted in the benzene ring to the ortho position and two substituents substituted on the same carbon in the aliphatic ring may be interpreted as "adjacent" groups to each other.
  • adjacent groups are bonded to each other to form a ring
  • substituent group means a substituted or unsubstituted hydrocarbon ring bonded to adjacent groups to form a ring; Or a substituted or unsubstituted heterocycle.
  • the ring is a substituted or unsubstituted hydrocarbon ring; Or a substituted or unsubstituted heterocycle.
  • the hydrocarbon ring may be an aromatic, aliphatic or aromatic and aliphatic condensed ring, and may be selected from the examples of the cycloalkyl group or the aryl group except the univalent hydrocarbon ring.
  • the aromatic ring may be monocyclic or polycyclic and may be selected from the examples of the aryl group except that it is not monovalent.
  • the hetero ring includes one or more non-carbon atoms and hetero atoms.
  • the hetero atom may include one or more atoms selected from the group consisting of O, N, Se, and S, and the like.
  • the heterocyclic ring may be monocyclic or polycyclic, and may be aromatic, aliphatic or aromatic and aliphatic condensed rings, and may be selected from the examples of the heteroaryl group except that it is not monovalent.
  • the formula (1) is represented by any one of the following formulas (2) to (4).
  • L1, L2 and Ar1 to Ar3 have the same definitions as in the above formula (1), and R and R 'are the same or different and each independently represents a substituted or unsubstituted alkyl group.
  • R and R ' are the same or different from each other and each independently an alkyl group.
  • R and R ' are the same or different from each other and are each independently a methyl group; An ethyl group; Propyl group; Or a butyl group.
  • L 1 and L 2 are the same or different from each other, and are each independently a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; A substituted or unsubstituted naphthylene group; Or a substituted or unsubstituted fluorenylene group.
  • L 1 and L 2 are the same or different from each other, and are each independently a direct bond; A phenylene group substituted or unsubstituted with an aryl group; A biphenyllylene group substituted or unsubstituted with an aryl group; A naphthylene group substituted or unsubstituted with an aryl group; Or a fluorenylene group substituted or unsubstituted with an aryl group or an alkyl group.
  • L 1 and L 2 are the same or different from each other, and are each independently a direct bond; A phenylene group; Biphenyllylene groups; Naphthylene group; Or a fluorenylene group substituted or unsubstituted with an alkyl group.
  • L 1 and L 2 are the same or different from each other, and are each independently a direct bond; A phenylene group; Biphenyllylene groups; Naphthylene group; Or a dimethylfluorenylene group.
  • L 1 and L 2 are the same or different from each other, and are each independently a direct bond; Or a phenylene group.
  • L1 is a direct bond; Or a substituted or unsubstituted arylene group.
  • L1 is a direct bond; A substituted or unsubstituted phenylene group; A substituted or unsubstituted biphenylene group; Or a substituted or unsubstituted fluorenylene group.
  • L1 is a direct bond; A phenylene group; Biphenyllylene groups; Or a fluorenylene group substituted or unsubstituted with an alkyl group.
  • L1 is a direct bond; A phenylene group; Biphenyllylene groups; Or a dimethylfluorenylene group.
  • L1 is a direct bond; Or a substituted or unsubstituted phenylene group.
  • L1 is a direct bond; A phenylene group; Or a biphenylene group.
  • L1 is a direct bond; Or a phenylene group.
  • L2 is a direct bond; Or a substituted or unsubstituted arylene group.
  • L2 is a direct bond; A substituted or unsubstituted phenylene group; Or a substituted or unsubstituted naphthylene group.
  • L2 is a direct bond; Or a substituted or unsubstituted phenylene group.
  • L2 is a direct bond; A phenylene group; Or a naphthylene group.
  • L2 is a direct bond
  • Ar 1 to Ar 3 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group.
  • Ar 1 to Ar 3 are the same or different and each independently represent a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group substituted or unsubstituted with an aryl group; An aryl group or a fluorenyl group substituted or unsubstituted with an alkyl group; A dibenzofurane group substituted or unsubstituted with an aryl group; A dibenzothiophene group substituted or unsubstituted with an aryl group; Or a carbazol group substituted or unsubstituted with an aryl group.
  • Ar1 to Ar3 are the same or different from each other, and are each independently a phenyl group; Naphthyl group; A biphenyl group; A terphenyl group; A fluorenyl group substituted or unsubstituted with a methyl group; A dibenzofurane group; A dibenzothiophene group; Or a carbazol group substituted or unsubstituted with a phenyl group.
  • Ar 3 is preferably a heterocyclic ring containing S or O rather than a heterocyclic ring containing N.
  • Ar 3 is dibenzofuran or dibenzothiophene group is more effective than the case where Ar 3 is a carbazole group, in terms of voltage, efficiency and life.
  • Ar1 and Ar2 are the same or different and are a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing N, S, or O, and Ar3 is a substituted or unsubstituted aryl group; Or a substituted or unsubstituted heterocyclic group containing S or O.
  • Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted dibenzofurane group; A substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted carbazole group, Ar 3 is a substituted or unsubstituted phenyl group; A substituted or unsubstituted naphthyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted terphenyl group; A substituted or unsubstituted fluorenyl group; A substituted or unsubstituted
  • Ar1 and Ar2 are the same or different and are each independently a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; A terphenyl group substituted or unsubstituted with an aryl group; An aryl group or a fluorenyl group substituted or unsubstituted with an alkyl group; A dibenzofurane group substituted or unsubstituted with an aryl group; A dibenzothiophene group substituted or unsubstituted with an aryl group; Or a carbazole group substituted or unsubstituted with an aryl group, Ar3 is a phenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl
  • Ar1 and Ar2 are the same or different from each other and are each independently a phenyl group; Naphthyl group; A biphenyl group; A terphenyl group; A fluorenyl group substituted or unsubstituted with a methyl group; A dibenzofurane group; A dibenzothiophene group; Or a carbazole group substituted or unsubstituted with a phenyl group
  • Ar3 is a phenyl group; Naphthyl group; A biphenyl group; A terphenyl group; A fluorenyl group substituted or unsubstituted with a methyl group; A dibenzofurane group; Or a dibenzothiophene group.
  • At least one of Ar1 to Ar3 is represented by the following formula (5).
  • X is O; S; CR3R4; Or NR5,
  • R3 to R5 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or may be bonded to each other to form a substituted or unsubstituted ring,
  • At least one of Ar1 and Ar2 is represented by the above formula (5).
  • Ar3 is represented by the formula (5).
  • Ar3 when Ar3 is the formula (5), X is O; S; Or CR3R4, R3 and R4 are the same or different and are each independently selected from the group consisting of hydrogen; A substituted or unsubstituted alkyl group; Or a substituted or unsubstituted aryl group, or are bonded to each other to form a substituted or unsubstituted ring.
  • At least one of Ar1 to Ar3 is dibenzofuran; Dibenzothiophene; A dimethylfluorene group; Or a phenylcarbazole group.
  • At least one of Ar1 and Ar2 is dibenzofuran; Dibenzothiophene; A dimethylfluorene group; Or a phenylcarbazole group, or Ar3 is dibenzofuran; Dibenzothiophene; Or a dimethylfluorene group.
  • At least one of Ar1 and Ar2 is dibenzofuran; Dibenzothiophene; Or a dimethylfluorene group.
  • Ar3 is a substituted or unsubstituted dibenzothiophene group; Or a substituted or unsubstituted dibenzofurane group.
  • Ar3 is a dibenzothiophene group; Or a dibenzofurane group.
  • At least one of Ar1 to Ar3 is represented by Formula 5, and the remainder is a substituted or unsubstituted aryl group.
  • At least one of Ar1 to Ar3 is represented by Formula 5, and the remaining is substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted terphenyl group.
  • At least one of Ar1 to Ar3 is a phenyl group substituted with an aryl group, and the remaining is substituted with an aryl group; A biphenyl group substituted or unsubstituted with an aryl group; A naphthyl group substituted or unsubstituted with an aryl group; Or a terphenyl group substituted or unsubstituted with an aryl group.
  • At least one of Ar1 to Ar3 is a phenyl group substituted with a naphthyl group or an unsubstituted naphthyl group; A biphenyl group; A naphthyl group substituted or unsubstituted with a phenyl group; Or a terphenyl group.
  • At least one of Ar1 to Ar3 is represented by Formula 5, and the remainder is a phenyl group; A biphenyl group; Naphthyl group; Or a terphenyl group.
  • Ar1 is represented by the above-described formula (5)
  • Ar2 and Ar3 are the same or different and each independently represents a substituted or unsubstituted aryl group.
  • Ar1 and Ar3 are the same or different and each is represented by the above-described formula (5), and Ar2 is a substituted or unsubstituted aryl group.
  • Ar3 is represented by the above formula (5), Ar1 and Ar2 are the same or different and each independently represents a substituted or unsubstituted aryl group.
  • R 3 to R 5 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted terphenyl group.
  • R 3 and R 4 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted alkyl group; A substituted or unsubstituted aryl group, or a bond to each other to form a substituted or unsubstituted ring.
  • R 3 and R 4 are the same or different from each other, and each independently hydrogen; A substituted or unsubstituted methyl group; A substituted or unsubstituted ethyl group; A substituted or unsubstituted propyl group; A substituted or unsubstituted butyl group; A substituted or unsubstituted phenyl group; A substituted or unsubstituted biphenyl group; A substituted or unsubstituted naphthyl group; Or a substituted or unsubstituted terphenyl group, or combine with each other to form a substituted or unsubstituted hydrocarbon ring.
  • R 3 and R 4 are the same or different from each other, and each independently hydrogen; Methyl group; An ethyl group; Propyl group; Butyl group; A phenyl group; A biphenyl group; Naphthyl group; Or a terphenyl group, or combine with each other to form a hydrocarbon ring.
  • R 3 and R 4 are the same or different from each other, and each independently hydrogen; Methyl group; Or a phenyl group, or combine with each other to form a fluorene ring.
  • R 3 and R 4 are the same or different from each other and are each independently a methyl group; Or a phenyl group, or combine with each other to form a fluorene ring.
  • R 3 and R 4 are the same as each other and are a methyl group; Or a phenyl group, or combine with each other to form a fluorene ring.
  • R 3 and R 4 are methyl groups.
  • R4 is hydrogen; Methyl group; An ethyl group; Propyl group; Propyl group; A phenyl group; A biphenyl group; Naphthyl group; Or a terphenyl group.
  • R4 is hydrogen; Or a substituted or unsubstituted aryl group.
  • R4 is hydrogen; A phenyl group; A biphenyl group; Naphthyl group; Or a terphenyl group.
  • R4 is a phenyl group; A biphenyl group; Naphthyl group; Or a terphenyl group.
  • R4 is a phenyl group.
  • the compound represented by Formula 1 is selected from the following structural formulas.
  • the compound according to one embodiment of the present application can be produced by a production method described below.
  • the core structure of the compound of Formula 1 may be prepared as shown in Reaction Schemes 1 to 3 below.
  • Substituent groups may be attached by methods known in the art, and the type, position or number of substituent groups may be varied according to techniques known in the art.
  • L 1, L 2, and Ar 1 to Ar 3 are the same as defined in Chemical Formula 1, and are a methyl group bonded to a fluorene group in Schemes 1 to 3;
  • a phenyl group An alkyl group such as an ethyl group or a propyl group instead of a spirofluorene group;
  • An aryl group such as a biphenyl group, a terphenyl group, or a naphthyl group; Or a spiro-linked hydrocarbon ring or a spiro-bonded heterocycle.
  • the present invention also provides an organic light emitting device comprising the above-described compound.
  • the first electrode A second electrode facing the first electrode; And at least one organic compound layer disposed between the first electrode and the second electrode, wherein at least one of the organic compound layers includes the compound.
  • a member When a member is referred to herein as being “on " another member, it includes not only a member in contact with another member but also another member between the two members.
  • the organic material layer of the organic light emitting device of the present application may have a single layer structure, but may have a multilayer structure in which two or more organic material layers are stacked.
  • the organic light emitting device may have a structure including a hole injecting layer, a hole transporting layer, a light emitting layer, an electron transporting layer, and an electron injecting layer as organic layers.
  • the structure of the organic light emitting device is not limited thereto and may include a smaller number of organic layers.
  • the organic layer includes a hole injection layer or a hole transport layer, and the hole injection layer or the hole transport layer includes the compound.
  • the organic material layer includes a hole injecting layer, a hole transporting layer, or a hole injecting and transporting layer, and the hole injecting layer, the hole transporting layer, or the hole injecting and transporting layer includes the above compound.
  • the organic layer includes an electron inhibiting layer, and the electron inhibiting layer includes the compound.
  • the electron suppression layer has a thickness of 10 ANGSTROM to 100 ANGSTROM.
  • the thickness of the electron inhibiting layer is 40 ANGSTROM to 60 ANGSTROM.
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode; At least one of the two or more organic layers includes two or more organic layers disposed between the light emitting layer and the first electrode or between the light emitting layer and the second electrode.
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode;
  • the organic compound layer provided between the light emitting layer and the first electrode is an electron suppressing layer, and the electron suppressing layer includes the compound.
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode;
  • the organic compound layer disposed between the light emitting layer and the first electrode is an electron suppressing layer
  • the electron suppressing layer includes the compound, and includes an organic compound layer between the electron suppressing layer and the first electrode
  • the organic compound layer is a hole transporting layer .
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode;
  • the organic compound layer provided between the emission layer and the first electrode is an electron suppressing layer, the electron suppressing layer includes the compound, and the organic compound layer includes the electron suppressing layer and the first electrode, to be.
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode;
  • the organic compound layer provided between the light emitting layer and the first electrode is an electron suppressing layer
  • the electron suppressing layer includes the compound
  • the organic compound layer includes two or more organic compound layers between the electron suppressing layer and the first electrode, A hole injection layer and a hole transport layer.
  • the organic light emitting device includes a first electrode; A second electrode facing the first electrode; And a light emitting layer provided between the first electrode and the second electrode;
  • the organic compound layer provided between the light emitting layer and the first electrode is an electron suppressing layer
  • the electron suppressing layer includes the compound
  • the first electron transporting layer includes the first organic compound layer between the electron suppressing layer and the first electrode
  • the first organic material layer includes a hole injection layer and a hole transporting layer, and at least two second organic material layers are provided between the light emitting layer and the second electrode
  • the second organic material layer includes a hole blocking layer, an electron injection layer, Injection and transport layer may be selected from two or more groups.
  • the two or more organic layers may be selected from the group consisting of a hole transporting layer, a hole injecting layer, a layer simultaneously transporting holes and holes, and an electron blocking layer.
  • the two or more organic layers may be selected from the group consisting of an electron transport layer, an electron injection layer, a layer that simultaneously transports electrons and electrons, and a hole blocking layer.
  • the organic material layer includes two or more electron transporting layers, and at least one of the two or more electron transporting layers includes the above compound.
  • the compound may be contained in one of the two or more electron transporting layers, and may be included in each of two or more electron transporting layers.
  • the materials other than the above compounds may be the same or different from each other.
  • the organic layer further includes a hole injection layer or a hole transport layer containing a compound containing an arylamino group, a carbazolyl group or a benzocarbazolyl group in addition to the organic compound layer containing the compound.
  • the organic light emitting device may be a normal type organic light emitting device in which an anode, at least one organic layer, and a cathode are sequentially stacked on a substrate.
  • the organic light emitting device may be an inverted type organic light emitting device in which a cathode, at least one organic material layer, and an anode are sequentially stacked on a substrate.
  • FIG. 1 shows a structure of an organic light emitting device in which a substrate 1, an anode 2, an organic material layer 3, and a cathode 4 are sequentially laminated.
  • Fig. 2 is a cross-sectional view showing a structure of a substrate 1, an anode 2, a hole injecting layer 5, a hole transporting layer 6, an electron restraining layer 7, a light emitting layer 8, a hole blocking layer 9, 10 and a cathode 4 are sequentially laminated on a substrate 1.
  • the compound is selectively removed from the hole injection layer 5, the hole transport layer 6, the electron restraining layer 7, the light emitting layer 8, the hole blocking layer 9 and the electron injection and transport layer 10 Layer.
  • the compound may be contained in at least one of the hole injecting layer, the hole transporting layer, the light emitting layer, and the electron transporting layer.
  • the organic light emitting device of the present application may be manufactured by materials and methods known in the art, except that one or more of the organic layers include the compound of the present application, i.e., the compound.
  • the organic layers may be formed of the same material or different materials.
  • the organic light emitting device of the present application can be manufactured by sequentially laminating a first electrode, an organic material layer, and a second electrode on a substrate.
  • a PVD (physical vapor deposition) method such as a sputtering method or an e-beam evaporation method
  • a metal or a metal oxide having conductivity or an alloy thereof is deposited on the substrate to form a positive electrode
  • an organic material layer including a hole injecting layer, a hole transporting layer, a light emitting layer and an electron transporting layer thereon depositing a material usable as a cathode thereon.
  • an organic light emitting device can be formed by sequentially depositing a cathode material, an organic material layer, and a cathode material on a substrate.
  • the compound of Formula 1 may be formed into an organic material layer by a solution coating method as well as a vacuum evaporation method in the production of an organic light emitting device.
  • the solution coating method refers to spin coating, dip coating, doctor blading, inkjet printing, screen printing, spraying, roll coating and the like, but is not limited thereto.
  • an organic light emitting device may be fabricated by sequentially depositing an organic material layer and a cathode material on a substrate from a cathode material (International Patent Application Publication No. 2003/012890).
  • the manufacturing method is not limited thereto.
  • the first electrode is an anode and the second electrode is a cathode.
  • the first electrode is a cathode and the second electrode is a cathode.
  • the cathode material a material having a large work function is preferably used so that hole injection can be smoothly conducted into the organic material layer.
  • the cathode material that can be used in the present invention include metals such as vanadium, chromium, copper, zinc, and gold, or alloys thereof; Metal oxides such as zinc oxide, indium oxide, indium tin oxide (ITO), and indium zinc oxide (IZO); ZnO: Al or SnO 2: a combination of a metal and an oxide such as Sb; Conductive polymers such as poly (3-methylthiophene), poly [3,4- (ethylene-1,2-dioxy) thiophene] (PEDOT), polypyrrole and polyaniline.
  • the negative electrode material is preferably a material having a small work function to facilitate electron injection into the organic material layer.
  • Specific examples of the negative electrode material include metals such as magnesium, calcium, sodium, potassium, titanium, indium, yttrium, lithium, gadolinium, aluminum, silver, tin and lead or alloys thereof; Layer structure materials such as LiF / Al or LiO 2 / Al, but are not limited thereto.
  • the hole injecting layer is a layer for injecting holes from an electrode.
  • the hole injecting material has a hole injecting effect, and has a hole injecting effect on the light emitting layer or a light emitting material.
  • a compound which prevents the migration of excitons to the electron injecting layer or the electron injecting material and is also excellent in the thin film forming ability is preferable. It is preferable that the highest occupied molecular orbital (HOMO) of the hole injecting material be between the work function of the anode material and the HOMO of the surrounding organic layer.
  • HOMO highest occupied molecular orbital
  • the hole injecting material include metal porphyrin, oligothiophene, arylamine-based organic materials, hexanitrile hexaazatriphenylene-based organic materials, quinacridone-based organic materials, and perylene- , Anthraquinone, polyaniline and polythiophene-based conductive polymers, but the present invention is not limited thereto.
  • the hole transport layer is a layer that transports holes from the hole injection layer 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 include arylamine-based organic materials, conductive polymers, and block copolymers having a conjugated portion and a non-conjugated portion together, but are not limited thereto.
  • the light emitting material is preferably a material capable of emitting light in the visible light region by transporting and receiving holes and electrons from the hole transporting layer and the electron transporting layer, respectively, and having good quantum efficiency for fluorescence or phosphorescence.
  • Specific examples include 8-hydroxy-quinoline aluminum complex (Alq 3 ); Carbazole-based compounds; Dimerized styryl compounds; BAlq; 10-hydroxybenzoquinoline-metal compounds; Compounds of the benzoxazole, benzothiazole and benzimidazole series; Polymers of poly (p-phenylenevinylene) (PPV) series; Spiro compounds; Polyfluorene, rubrene, and the like, but are not limited thereto.
  • 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 compound.
  • Specific examples of the condensed aromatic ring derivatives include anthracene derivatives, pyrene derivatives, naphthalene derivatives, pentacene derivatives, phenanthrene compounds, and fluoranthene compounds.
  • Examples of heterocycle-containing compounds include compounds, dibenzofuran derivatives, ladder furan compounds , Pyrimidine derivatives, and the like, but are not limited thereto.
  • the electron transporting layer is a layer that receives electrons from the electron injecting layer and transports electrons to the light emitting layer.
  • the electron transporting material is a material capable of transferring electrons from the cathode well to the light emitting layer. Suitable. Specific examples include an Al complex of 8-hydroxyquinoline; Complexes containing Alq 3 ; Organic radical compounds; Hydroxyflavone-metal complexes, and the like, but are not limited thereto.
  • the electron transporting layer can be used with any desired cathode material as used according to the prior art.
  • an example of a suitable cathode material is a conventional material having a low work function followed by an aluminum layer or a silver layer. Specifically cesium, barium, calcium, ytterbium and samarium, in each case followed by an aluminum layer or a silver layer.
  • the electron injection layer is a layer for injecting electrons from the electrode.
  • the electron injection layer has an ability to transport electrons, has an electron injection effect from the cathode, and has an excellent electron injection effect with respect to the light emitting layer or the light emitting material.
  • a compound which prevents migration to a layer and is excellent in a thin film forming ability is preferable.
  • Specific examples thereof include fluorenone, anthraquinodimethane, diphenoquinone, thiopyran dioxide, oxazole, oxadiazole, triazole, imidazole, perylenetetracarboxylic acid, preorenylidene methane, A complex compound and a nitrogen-containing five-membered ring derivative, 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- Tris (8-hydroxyquinolinato) aluminum, tris (2-methyl-8-hydroxyquinolinato) aluminum, tris (8- hydroxyquinolinato) gallium, bis (10- Quinolinato) beryllium, bis (10-hydroxybenzo [h] quinolinato) zinc, bis (2-methyl-8- quinolinato) chlorogallium, bis (2-methyl-8-quinolinato) (2-naphtholato) gallium, and the like, But is not limited thereto.
  • the hole blocking layer prevents holes from reaching the cathode, and may be formed under the same conditions as those of the hole injecting layer. Specific examples thereof include, but are not limited to, oxadiazole derivatives, triazole derivatives, phenanthroline derivatives, BCP, aluminum complexes and the like.
  • the organic light emitting device according to the present invention may be of a top emission type, a back emission type, or a both-side emission type, depending on the material used.
  • furan (3.5 g, 14.23 mmol) was added to a 500 ml round-bottomed flask in a nitrogen atmosphere at -78 [deg.] C with tetrahydrofuran
  • 2M aqueous potassium carbonate solution 100 ml was added, tetrakis- (triphenylphosphine) palladium (0.49 g, 0.43 mmol) was added and the mixture was heated with stirring for 6 hours.
  • a substituent which binds to the fluorene group in the production of the above Compounds A to E and Production Examples 1 to 11; A substituent bonded to an amine group; And the substituent bonded to Br may be adjusted to prepare the compound of formula (1).
  • the glass substrate coated with ITO (indium tin oxide) thin film with a thickness of 1,000 ⁇ was immersed in distilled water containing detergent and washed with ultrasonic waves. At this time, Fischer Co. product was used as a detergent, and distilled water, which was secondly filtered with a filter of Millipore Co., was used as distilled water.
  • the ITO was washed for 30 minutes and then washed twice with distilled water and ultrasonically cleaned for 10 minutes. After the distilled water was washed, it was ultrasonically washed with a solvent of isopropyl alcohol, acetone, and methanol, dried, and then transported to a plasma cleaner. Further, the substrate was cleaned using oxygen plasma for 5 minutes, and then the substrate was transported by a vacuum evaporator.
  • the ITO transparent electrode thus prepared was thermally vacuum-deposited to a thickness of 100 ANGSTROM so as to have a ratio of the following compound HI1 and the following compound HI2 in a molar ratio of 98: 2, thereby forming a hole injection layer.
  • a compound (1150 ANGSTROM) represented by the following formula (HT1) was vacuum-deposited on the hole injection layer to form a hole transport layer.
  • Compound 1 of Preparation Example 1 prepared above was vacuum deposited on the hole transport layer to a thickness of 50 ANGSTROM to form an electron inhibition layer.
  • a compound represented by the following formula (BH) and a compound represented by the following formula (BD) were vacuum deposited on the electron suppression layer to a thickness of 200 angstroms at a weight ratio of 50: 1 to form a light emitting layer.
  • a hole blocking layer was formed on the light emitting layer by vacuum evaporation of a compound represented by the following formula HB1 to a film thickness of 50 ANGSTROM.
  • a compound represented by the following formula (ET1) and a compound represented by the following formula (LiQ) were vacuum deposited on the hole blocking layer at a weight ratio of 1: 1 to form an electron injecting and transporting layer having a thickness of 30 ⁇ .
  • Lithium fluoride (LiF) and aluminum having a thickness of 1,000 ⁇ were sequentially deposited on the electron injecting and transporting layer to form a cathode.
  • An organic light emitting device was prepared in the same manner as in Example 1-1 except that the compound 2 was used in place of the compound 1 in Production Example 1.
  • An organic light emitting device was fabricated in the same manner as in Example 1-1 except that the compound 3 was used in place of the compound 1 in Production Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1-1 except that the compound 4 was used in place of the compound 1 in Production Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1-1 except that the compound 5 was used in place of the compound 1 in Production Example 1.
  • An organic luminescent device was prepared in the same manner as in Example 1-1, except that the compound 6 was used in place of the compound 1 of Preparation Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1-1 except that the compound 7 was used in place of the compound 1 in Production Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1-1 except that the compound 8 was used in place of the compound 1 in Production Example 1.
  • An organic light emitting device was fabricated in the same manner as in Example 1-1 except that the compound 9 was used in place of the compound 1 in Production Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1-1 except that Compound 10 was used in place of Compound 1 of Preparation Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1-1, except that the compound 11 was used in place of the compound 1 in Production Example 1.
  • An organic luminescent device was prepared in the same manner as in Example 1-1 except that the following compound EB1 was used in place of the compound of Preparation Example 1.
  • An organic light emitting device was prepared in the same manner as in Example 1-1 except that the following compound EB2 was used in place of the compound of Preparation Example 1.
  • An organic luminescent device was prepared in the same manner as in Example 1-1, except that the following compound EB4 was used in place of the compound of Preparation Example 1.
  • An organic luminescence device was prepared in the same manner as in Example 1-1, except that the following compound EB5 was used in place of the compound of Preparation Example 1.
  • An organic luminescent device was prepared in the same manner as in Example 1-1 except that the following compound EB6 was used in place of the compound of Preparation Example 1.
  • An organic luminescent device was prepared in the same manner as in Example 1-1, except that the following compound EB7 was used in place of the compound of Preparation Example 1.
  • T95 means the time required for the luminance to decrease from the initial luminance (1600 nits) to 95%.
  • the organic light emitting device using the compound of the present invention as the electron suppressing layer exhibited excellent characteristics in terms of efficiency, driving voltage and stability of the organic light emitting device.
  • Examples 1-1 to 1-11 the substitution of the aryl group at the 2-position of the fluorene showed high efficiency characteristics.
  • the dibenzofuran and dibenzothiophene substituted materials were used as the electron suppression layer, And the long-life characteristics. This is because dibenzofuran and dibenzothiophene are connected to a substituent and the HOMO value is deepened, so that the barrier to the interface of the light emitting layer is reduced and the stability to electrons is greatly increased.
  • Comparative Examples 1 and 2 had a structure in which only an arylamine group was connected to the 3-position of the fluorene-based core and had no substituent at the 2-position. Thus, the compound was inferior to the compound of the present invention in terms of efficiency, driving voltage and stability.
  • Comparative Example 4 is a structure in which fluorine atoms 3 and 6 are arylamine groups, and No. 2 and No. 7 are substituted with aryl groups, and the number of amines is 4, which greatly increases the HOMO value, And the balance of the device is completely broken.
  • Comparative Example 7 is a material in which the amine group and the aryl group are symmetrically connected at the 2nd and 7th positions of the fluorene group, which is not preferable to the compound of the present invention.
  • the compound of the present invention is excellent in electron blocking ability and applicable to organic light emitting devices.

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Abstract

La présente invention concerne un composé représenté par la formule chimique (1) et un dispositif électroluminescent organique le comprenant.
PCT/KR2019/001116 2018-01-25 2019-01-25 Composé et dispositif électroluminescent organique le comprenant WO2019147077A1 (fr)

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Cited By (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111253264A (zh) * 2018-11-30 2020-06-09 关东化学株式会社 2-取代芴化合物、含该化合物的空穴传输材料及空穴传输层中含该化合物的有机电子器件
CN113173858A (zh) * 2021-04-21 2021-07-27 陕西莱特迈思光电材料有限公司 含氮化合物、电子元件和电子装置

Families Citing this family (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
KR102632832B1 (ko) * 2018-06-27 2024-02-05 주식회사 동진쎄미켐 신규 화합물 및 이를 포함하는 유기발광 소자
KR102628804B1 (ko) * 2018-07-10 2024-01-24 주식회사 동진쎄미켐 신규 화합물 및 이를 포함하는 유기발광 소자
CN113372313B (zh) * 2021-07-02 2022-08-12 长春海谱润斯科技股份有限公司 一种三芳胺化合物及其有机电致发光器件

Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015162912A1 (fr) * 2014-04-21 2015-10-29 出光興産株式会社 Élément électroluminescent organique
KR20170088313A (ko) * 2016-01-22 2017-08-01 주식회사 엘지화학 아민계 화합물 및 이를 포함하는 유기 발광 소자
KR20170136916A (ko) * 2016-06-02 2017-12-12 주식회사 엘지화학 유기 발광 소자
KR20180010132A (ko) * 2016-07-20 2018-01-30 주식회사 엘지화학 다중고리 화합물 및 이를 포함하는 유기 발광 소자
KR20180043744A (ko) * 2016-10-20 2018-04-30 주식회사 엘지화학 다중고리 화합물 및 이를 포함하는 유기 발광 소자
KR20180063707A (ko) * 2016-12-02 2018-06-12 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기발광소자

Family Cites Families (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
DE10135513B4 (de) 2001-07-20 2005-02-24 Novaled Gmbh Lichtemittierendes Bauelement mit organischen Schichten

Patent Citations (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2015162912A1 (fr) * 2014-04-21 2015-10-29 出光興産株式会社 Élément électroluminescent organique
KR20170088313A (ko) * 2016-01-22 2017-08-01 주식회사 엘지화학 아민계 화합물 및 이를 포함하는 유기 발광 소자
KR20170136916A (ko) * 2016-06-02 2017-12-12 주식회사 엘지화학 유기 발광 소자
KR20180010132A (ko) * 2016-07-20 2018-01-30 주식회사 엘지화학 다중고리 화합물 및 이를 포함하는 유기 발광 소자
KR20180043744A (ko) * 2016-10-20 2018-04-30 주식회사 엘지화학 다중고리 화합물 및 이를 포함하는 유기 발광 소자
KR20180063707A (ko) * 2016-12-02 2018-06-12 (주)피엔에이치테크 유기발광 화합물 및 이를 포함하는 유기발광소자

Cited By (6)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN111253264A (zh) * 2018-11-30 2020-06-09 关东化学株式会社 2-取代芴化合物、含该化合物的空穴传输材料及空穴传输层中含该化合物的有机电子器件
CN113173858A (zh) * 2021-04-21 2021-07-27 陕西莱特迈思光电材料有限公司 含氮化合物、电子元件和电子装置
WO2022222646A1 (fr) * 2021-04-21 2022-10-27 陕西莱特迈思光电材料有限公司 Composé contenant de l'azote, composant électronique et dispositif électronique
KR20230051301A (ko) * 2021-04-21 2023-04-17 산시 라이트 옵토일렉스로닉스 머터리얼 코포레이션 리미티드 질소 함유 화합물, 전자 소자 및 전자 장치
US11795389B2 (en) 2021-04-21 2023-10-24 Shaanxi Lighte Optoelectronics Material Co., Ltd. Nitrogen-containing compound, electronic component, and electronic device
KR102612622B1 (ko) 2021-04-21 2023-12-13 산시 라이트 옵토일렉스로닉스 머터리얼 코포레이션 리미티드 질소 함유 화합물, 전자 소자 및 전자 장치

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