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WO2018179482A1 - Composé pour élément électroluminescent organique et élément électroluminescent organique - Google Patents

Composé pour élément électroluminescent organique et élément électroluminescent organique Download PDF

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WO2018179482A1
WO2018179482A1 PCT/JP2017/030908 JP2017030908W WO2018179482A1 WO 2018179482 A1 WO2018179482 A1 WO 2018179482A1 JP 2017030908 W JP2017030908 W JP 2017030908W WO 2018179482 A1 WO2018179482 A1 WO 2018179482A1
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compound
group
organic
layer
organic electroluminescent
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直子 矢内
桐生 池部
純一 星野
友美 岩本
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TDK Corp
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C22/00—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom
    • C07C22/02—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings
    • C07C22/04—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings
    • C07C22/08—Cyclic compounds containing halogen atoms bound to an acyclic carbon atom having unsaturation in the rings containing six-membered aromatic rings containing fluorine
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C25/00—Compounds containing at least one halogen atom bound to a six-membered aromatic ring
    • C07C25/18—Polycyclic aromatic halogenated hydrocarbons
    • C07C25/22—Polycyclic aromatic halogenated hydrocarbons with condensed rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/50—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings
    • C07C255/51—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of non-condensed six-membered aromatic rings containing at least two cyano groups bound to the carbon skeleton
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C255/00—Carboxylic acid nitriles
    • C07C255/49—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton
    • C07C255/52—Carboxylic acid nitriles having cyano groups bound to carbon atoms of six-membered aromatic rings of a carbon skeleton to carbon atoms of six-membered aromatic rings being part of condensed ring systems
    • 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]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H10K50/12—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers comprising dopants

Definitions

  • the present invention relates to a compound for organic electroluminescence device and an organic electroluminescence device.
  • An organic electroluminescent element is an electronic element in which a thin film containing a luminescent organic compound is sandwiched between an anode and a cathode. By injecting holes and electrons from each electrode, excitons of the light-emitting organic compound are generated, and the organic electroluminescent element emits light when the excitons return to the ground state.
  • an element structure of an organic electroluminescent element As an element structure of an organic electroluminescent element, a two-layer type of a hole transport layer and an electron transport light-emitting layer, or a three-layer type of a hole transport layer, a light-emitting layer, and an electron transport layer has been studied. At present, in order to further enhance the recombination efficiency of injected holes and electrons, a structure in which a hole injection layer and an electron injection layer are inserted between an anode and a hole transport layer and a cathode and an electron transport layer, respectively, is the mainstream. It has become.
  • Organic electroluminescent elements are expected to be a technology for realizing light-emitting devices that are excellent in contrast, responsiveness, and viewing angle, low power consumption, thin and light, and are actively researched.
  • the light emitting efficiency and continuous drive life of the current elements are not sufficient in practical use, and further high-efficiency light emission and longer life are required.
  • these problems have not been sufficiently solved, especially for blue light emitting devices. There is a strong demand for improved properties of materials.
  • Patent Document 1 reports an example in which a benzofluorene having a diarylamino group and a dibenzofluorene derivative are used as a light emitting layer dopant.
  • Patent Documents 2 and 3 report examples in which a dibenzo [c, g] fluorene derivative having an aryl group is used as a light emitting layer host material.
  • Patent Document 4 reports a dibenzo [c, g] fluorene derivative substituted with a diarylamino group or an electron transporting substance.
  • the present invention has been made in view of the above circumstances, and when used as a constituent material of an organic electroluminescence device, the compound for organic electroluminescence device and organic electroluminescence exhibiting long-life and high-purity blue light emission.
  • An object is to provide an element.
  • the present invention contains a compound for an organic electroluminescence device represented by the following general formula (1) and the compound for an organic electroluminescence device alone or as a component of a mixture.
  • An organic electroluminescent device is provided.
  • Y 1 and Y 2 are each independently a linear or branched alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • X 1 and X 2 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituent represented by any one of the following general formulas (2), (3), and (4). Yes, at least one of X 1 and X 2 is a substituent represented by any one of the following general formulas (2), (3), and (4).
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.
  • m is an integer of 1 to 2.
  • Ar 2 is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.
  • n is an integer of 1 to 5.
  • Ar 3 is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.
  • p is an integer of 1 to 2.
  • a dopant having a triarylamino group generally exhibits high fluorescence intensity, has a high highest occupied orbital (HOMO), and efficiently generates hole traps and charge recombination on the dopant.
  • An organic electroluminescent element can be realized. In such an organic electroluminescence device, it is generally considered that intensive charge recombination and subsequent dopant excitation and emission occur in the light emitting layer in the vicinity of the hole transport layer.
  • the charge recombination region is likely to be concentrated near the interface between the light emitting layer and the hole transport layer. It is considered that there is a possibility that the decrease in
  • the present inventors have a low minimum orbital (LUMO), and in an organic electroluminescent device using an electron-accepting light-emitting dopant, there is a high possibility of charge recombination in the vicinity of the interface between the light-emitting layer and the electron transport layer, We thought that the drive life could be improved because charge recombination near the interface between the light emitting layer and the hole transport layer could be suppressed.
  • LUMO low minimum orbital
  • At least one aryl group having a cyano group, a fluoro group, or a trifluoromethyl group is dibenzo [c, g] fluorene. It has a structure substituted at the 9th and 9th positions.
  • the dibenzo [c, g] fluorene derivative of the present invention has a low LUMO and a property of easily trapping electrons as compared with a polycyclic aromatic compound generally used as a light emitting layer host material. It can be considered that charge recombination in the vicinity of the interface between the hole transport layer and the hole transport layer can be suppressed, and a decrease in luminance accompanying driving of the element can be suppressed.
  • the driving lifetime is caused by the longer wavelength of the emission spectrum, that is, the color purity of blue light emission accompanying the decrease in LUMO, and the interaction with peripheral materials in the device.
  • the organic electroluminescence element cannot be extended in life and color purity can be improved.
  • the aryl group having a cyano group, a fluoro group, or a trifluoromethyl group imparts an appropriate electron accepting property to the dibenzo [c, g] fluorene of the present invention, and emits blue light having a high color purity around 430 nm to 470 nm and an organic electric field. The lifetime of the light emitting element can be extended.
  • X 1 and X 2 are each independently a substituent represented by any one of the general formulas (2), (3), and (4). Is preferred.
  • a compound for an organic electroluminescence device having such a structure has a suitable emission wavelength and electron acceptability that enable both high color purity and a long driving life as a blue light emitting dopant.
  • Ar 1 , Ar 2 , and Ar 3 are preferably a substituted or unsubstituted phenyl group, naphthyl group, or biphenyl group.
  • Ar 1 , Ar 2 , and Ar 3 are the above substituents, it is possible to realize blue light emission with higher color purity.
  • the compound is easy to synthesize, it is possible to produce a compound for an organic electroluminescence device with few impurities, and thus it is possible to obtain an organic electroluminescence device with a long driving life.
  • the organic layer has a light emitting layer, and the light emitting layer contains the compound.
  • the light emitting layer has a host material and a dopant, and the dopant contains the compound.
  • an organic electroluminescent device since the dopant has an appropriate electron accepting property, the concentration of charge recombination at the interface between the light emitting layer and the hole transport layer and the interaction with the surrounding materials can be suppressed, and a long driving life can be achieved. It is possible to realize. Moreover, such an organic electroluminescent element emits blue light with high color purity.
  • the organic layer has at least one of a hole injection layer or a hole transport layer, and at least a part of the hole injection layer or the hole transport layer functions as an electron acceptor, Or it is preferable that an organic compound is included.
  • the dopant sufficiently captures the carrier and counters the carrier. Is sufficiently supplied to the dopant in the light emitting layer.
  • both carriers do not recombine quickly, a compound in a radical state corresponding to excess carriers exists in the device, which inhibits light emission and causes a short life.
  • a compound that functions as an electron acceptor can generate holes by extracting electrons from an adjacent organic substance, in an organic electroluminescent device in which at least a part of a hole injection layer or a hole transport layer contains an electron acceptor, an anode
  • the injection barrier from the injection of holes to the light emitting layer can be significantly reduced.
  • holes can be sufficiently supplied to the electron-accepting dopant used in the organic electroluminescence device of the present invention, light emission with high efficiency and long life is possible.
  • an organic electroluminescent element that emits blue light with a long lifetime and high color purity.
  • FIG. 1 is a diagram showing a 1 HNMR spectrum of a compound (11) of the present invention of Synthesis Example 1.
  • FIG. It is a figure which shows the 13 CNMR spectrum of the compound (11) of this invention of the synthesis example 1.
  • 1 is a diagram showing a 1 HNMR spectrum of a compound (12) of the present invention in Synthesis Example 2.
  • FIG. It is a figure which shows the 13 CNMR spectrum of the compound (12) of this invention of the synthesis example 2.
  • 4 is a diagram showing a 1 HNMR spectrum of a compound (13) of the present invention in Synthesis Example 3.
  • the compound for organic electroluminescent elements is a dibenzo [c, g] fluorene compound having a specific structure represented by the following general formula (1).
  • Y 1 and Y 2 are each independently a linear or branched alkyl group having 1 to 10 carbon atoms, or a substituted or unsubstituted aryl group having 6 to 12 carbon atoms.
  • X 1 and X 2 are each independently a substituted or unsubstituted aryl group having 6 to 20 carbon atoms, or a substituent represented by any one of the following general formulas (2), (3), and (4). Yes, at least one of X 1 and X 2 is a substituent represented by any one of the following general formulas (2), (3), and (4).
  • Ar 1 is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.
  • m is an integer of 1 to 2.
  • Ar 2 is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.
  • n is an integer of 1 to 5.
  • Ar 3 is a substituted or unsubstituted aryl group having 6 to 16 carbon atoms.
  • p is an integer of 1 to 2.
  • Y 1 and Y 2 are each independently a linear or branched alkyl group having 1 to 10 carbon atoms, specifically, a methyl group, an ethyl group, a linear or branched group.
  • a methyl group specifically, an ethyl group, a linear or branched group.
  • Propyl group butyl group, pentyl group, hexyl group, heptyl group, octyl group, nonyl group and decyl group.
  • Y 1 and Y 2 are each independently a substituted or unsubstituted aryl group having 6 to 12 carbon atoms, and specific examples thereof include a phenyl group, a naphthyl group, and a biphenyl group. It is done.
  • Y 1 and Y 2 are preferably a methyl group, an ethyl group, a propyl group, a butyl group, a phenyl group, a naphthyl group, or a biphenylyl group from the viewpoint of the stability of the compound and the organic electroluminescent device and the ease of synthesis. Group, phenyl group, and biphenylyl group are more preferable.
  • Y 1 and Y 2 are each independently a phenyl group or a naphthyl group, Y 1 and Y 2 may be bonded to form a cyclic structure.
  • Y 1 and Y 2 may be the same or different.
  • the aryl group may be further substituted with a substituent.
  • substituents include an aryl group, an alkyl group, an alkoxy group, an aryloxy group, a halogeno group, and a silyl group.
  • an aryl group and an alkyl group are preferable from the viewpoint of the stability of the organic electroluminescent device, and a phenyl group, a naphthyl group, a biphenylyl group, a methyl group, an ethyl group, a propyl group, and a butyl group are more preferable.
  • X 1 and X 2 which are not a substituent represented by any one of the general formulas (2), (3) and (4) are substituted or unsubstituted 6 to 6 carbon atoms.
  • 20 aryl groups and specifically include phenyl, naphthyl, biphenylyl, fluorenyl, benzofluoryl, phenanthryl, anthracenyl, pyrenyl, chrysenyl, terphenylyl, tetracenyl and the like.
  • aryl group of X 1 and X 2 a phenyl group, a naphthyl group, a biphenylyl group, a fluorenyl group, a benzofluoryl group, and a phenanthryl group are preferable, and a phenyl group, a naphthyl group, and a biphenylyl group are preferable because blue light emission with high color purity can be obtained. Groups are more preferred.
  • the aryl group may be further substituted with a substituent.
  • substituents include an aryl group, an alkyl group, an alkoxy group, an aryloxy group, a halogeno group, and a silyl group.
  • an aryl group and an alkyl group are preferred from the viewpoint of obtaining blue light emission with high stability and stability of the organic electroluminescent device, and phenyl group, naphthyl group, biphenylyl group, methyl group, ethyl group, A propyl group and a butyl group are more preferable.
  • At least one of X 1 and X 2 is represented by any one of the general formulas (2), (3), and (4).
  • X 1 and X 2 are preferably each independently a substituent represented by any of the general formulas (2), (3), and (4).
  • the compound for an organic electroluminescence device having such a structure has a suitable emission wavelength and electron acceptability that enable both high color purity and a long drive life as a blue light emitting dopant.
  • At least one of X 1 and X 2 is preferably a substituent represented by the general formula (2).
  • the compound for an organic electroluminescence device having such a structure exhibits high luminous efficiency in addition to high color purity and a long driving life as a blue light emitting dopant.
  • X 1 and X 2 may be the same or different.
  • Ar 1 , Ar 2 , and Ar 3 are each independently a substituted or unsubstituted aryl group having 6 to 16 carbon atoms, specifically, examples thereof include a phenyl group, a naphthyl group, a biphenylyl group, a fluorenyl group, a phenanthryl group, an anthracenyl group, and a pyrenyl group.
  • a phenyl group, a naphthyl group, a biphenylyl group, and a fluorenyl group are preferable, and a phenyl group, a naphthyl group, and a biphenylyl group are more preferable because blue light emission with high color purity can be obtained. Since such a structure is easy to synthesize, it is possible to produce a compound for an organic electroluminescence device with few impurities, and thus an organic electroluminescence device with a long driving life can be obtained.
  • the aryl group may be further substituted with a substituent.
  • substituents include an aryl group, an alkyl group, an alkoxy group, an aryloxy group, a halogeno group, and a silyl group.
  • an aryl group and an alkyl group are preferable from the viewpoint that the compound and the organic electroluminescence device can be stable and blue light emission with high color purity is obtained, and a phenyl group, a naphthyl group, a biphenylyl group, a methyl group, an ethyl group are preferable.
  • a group, a propyl group, and a butyl group are more preferable.
  • n is an integer of 1 to 5
  • p is 1 to 2. It is an integer. According to such a structure, blue light emission with high color purity is possible.
  • the molecular weight of the compound according to the present embodiment is not particularly limited, but it is preferable that the molecular weight is 1300 or less in consideration of the element production process. This is because a compound having a molecular weight of 1300 or more is difficult to synthesize due to a decrease in solubility, and it is difficult to produce an organic electroluminescent device by a coating process. Further, even when an organic electroluminescent element is produced by a vapor deposition process, the vapor deposition temperature becomes high, which may cause decomposition of the material.
  • Preferable examples of the compound for organic electroluminescence device represented by the general formula (1) according to this embodiment include the following formulas (I-1) to (I-36), (II-1) to (II- 31).
  • FIG. 1 is a schematic cross-sectional view showing an example of an organic electroluminescent element according to this embodiment.
  • the organic electroluminescent element 1 shown in FIG. 1 includes a hole injection layer 4, a hole transport layer 5, a light emitting layer 6, and two electrodes (first electrode 3 and second electrode 9) arranged to face each other.
  • the electron transport layer 7 and the electron injection layer 8 are sandwiched.
  • the hole injection layer 4, the hole transport layer 5, the light emitting layer 6, the electron transport layer 7, and the electron injection layer 8 are all organic layers, and are stacked in this order from the first electrode 3 side.
  • the electron injection layer 8 may be an inorganic layer (metal layer, metal compound layer, etc.).
  • the first electrode 3 is formed on the substrate 2, but the stacking order from the substrate 2 side may be reversed. That is, even if the second electrode 9, the electron injection layer 8, the electron transport layer 7, the light emitting layer 6, the hole transport layer 5, the hole injection layer 4, and the first electrode 3 are stacked in this order from the substrate 2 side. Good.
  • organic electroluminescent element compound used in the present embodiment may be contained in any of the layers described above, but is preferably contained in the light emitting layer 6.
  • the first electrode 3 and the second electrode 9 function as a hole injecting electrode (anode) and an electron injecting electrode (cathode), respectively.
  • anode anode
  • cathode an electron injecting electrode
  • the preferred thicknesses of the hole injection layer 4, the hole transport layer 5, the light emitting layer 6, the electron transport layer 7 and the electron injection layer 8 are all 1 to 200 nm.
  • the substrate 2 can be used without particular limitation as long as it is provided in a conventional organic electroluminescence device, and is an amorphous substrate such as glass or quartz, Si, GaAs, ZnSe, ZnS, GaP.
  • a crystal substrate such as InP or a metal substrate such as Mo, Al, Pt, Ir, Au, Pd, or SUS can be used.
  • a thin film made of a crystalline or amorphous ceramic, metal, organic substance or the like formed on a predetermined substrate may be used.
  • the substrate 2 side is the light extraction side
  • a transparent substrate such as glass or quartz
  • an inexpensive glass transparent substrate may be provided with a color filter film, a color conversion film containing a fluorescent material, a dielectric reflection film, or the like for adjusting the emission color.
  • the first electrode 3 functions as a hole injection electrode (anode). Therefore, the material of the first electrode 3 can be used without particular limitation as long as it is provided in the conventional organic electroluminescent element, but it can be used efficiently and uniformly for the first electrode 3. A material capable of applying an electric field to is preferable.
  • the transmittance at a wavelength of 400 nm to 700 nm, which is the emission wavelength region of the organic electroluminescence element, in particular, the transmittance of the first electrode 3 at the wavelength of each RGB color is 50%. Preferably, it is 80% or more, more preferably 90% or more.
  • the transmittance of the first electrode 3 is less than 50%, the light emission from the light emitting layer 6 is attenuated, and the luminance necessary for image display cannot be obtained.
  • the 1st electrode 3 with high light transmittance can be comprised using the transparent conductive film comprised with various oxides.
  • a material indium oxide (In 2 O 3 ), tin oxide (SnO 2 ), zinc oxide (ZnO), tin-doped indium oxide (ITO), zinc-doped indium oxide (IZO), and the like are preferable. It is particularly preferable in that a thin film having a uniform in-plane specific resistance can be easily obtained.
  • the film thickness of the first electrode 3 is preferably determined in consideration of the light transmittance described above.
  • the film thickness is preferably 10 to 500 nm, more preferably 30 to 300 nm.
  • the film thickness of the first electrode 3 exceeds 500 nm, the light transmittance becomes insufficient and the first electrode 3 may be peeled off from the substrate 2 in some cases.
  • the light transmittance is improved as the film thickness is decreased.
  • the film thickness is less than 10 nm, the resistance increases and the driving voltage of the organic electroluminescent element tends to increase.
  • the second electrode 9 functions as an electron injection electrode (cathode).
  • the material of the second electrode 9 can be used without particular limitation as long as it is provided in a conventional organic electroluminescent device, and examples thereof include metal materials, organometallic complexes, and metal compounds. In order to efficiently and reliably inject electrons into the light emitting layer 6, it is preferable to use a material having a relatively low work function, and it may be transparent.
  • the metal material constituting the second electrode 9 include alkali metals such as Li, Na, K or Cs, alkaline earth metals such as Mg, Ca, Sr or Ba, or Al (aluminum). .
  • alkali metals such as Li, Na, K or Cs
  • alkaline earth metals such as Mg, Ca, Sr or Ba
  • Al (aluminum) a metal having properties similar to those of an alkali metal or alkaline earth metal such as La, Ce, Sn, Zn, or Zr
  • oxides or halides of the above metal materials can also be used. Further, it may be a mixture or alloy containing the above materials, and a plurality of these may be laminated.
  • the film thickness of the second electrode 9 only needs to be such that electrons can be uniformly injected, and may be 0.1 nm or more.
  • An auxiliary electrode may be provided on the second electrode 9.
  • the electron injection efficiency to the light emitting layer 6 can be improved, and the penetration
  • a material for the auxiliary electrode a general metal can be used because there is no restriction on work function and charge injection capability. However, it is preferable to use a metal having high conductivity and easy handling.
  • the second electrode 9 includes an organic material, it is preferable to select appropriately according to the type and adhesion of the organic material.
  • auxiliary electrode examples include Al, Ag, In, Ti, Cu, Au, Mo, W, Pt, Pd, and Ni.
  • a low-resistance metal such as Al and Ag. Electron injection efficiency can be further increased.
  • a metal compound such as TiN, higher sealing performance can be realized. These materials may be used alone or in combination of two or more. Moreover, when using 2 or more types of metals, you may use as an alloy.
  • Such an auxiliary electrode can be formed by, for example, a vacuum deposition method or the like.
  • the hole injection layer 4 is a layer containing a compound having a function of facilitating hole injection from the first electrode 3. Specifically, it can be formed using at least one kind of hydrocarbon-based material such as triarylamine derivative, carbazole derivative, anthracene derivative, azatriphenylene derivative, phthalocyanine derivative, polyaniline / organic acid, polythiophene / polymer acid, and the like. it can.
  • hydrocarbon-based material such as triarylamine derivative, carbazole derivative, anthracene derivative, azatriphenylene derivative, phthalocyanine derivative, polyaniline / organic acid, polythiophene / polymer acid, and the like. it can.
  • the hole transport layer 5 is a layer containing a compound having a function of transporting injected holes to the light emitting layer 6 and a function of preventing electrons in the light emitting layer 6 from being injected into the hole transport layer 5.
  • the hole transport layer 5 uses at least one kind of hydrocarbon compound such as triarylamine derivative, triarylmethane derivative, stilbene derivative, polysilane derivative, polyphenylene vinylene and derivative thereof, polythiophene and derivative thereof, carbazole derivative, or anthracene derivative. Can be formed.
  • the hole injection layer 4 and the hole transport layer 5 can be further functionally separated into a plurality of layers.
  • hole injection layer 4 or the hole transport layer 5 When a material having a high work function such as a carbazole derivative or a hydrocarbon-based material is used for the hole injection layer 4 or the hole transport layer 5, hole injection from the anode 3 to the hole injection layer 4 or from the hole injection layer 4 to the hole transport layer 5 is performed. Although the barrier is increased, holes can be forcibly generated by containing an inorganic compound or an organic material functioning as an electron acceptor in a part of the hole injection layer 4 or the hole transport layer 5. The injection barrier can be lowered.
  • a material having a high work function such as a carbazole derivative or a hydrocarbon-based material
  • an inorganic compound antimony chloride, vanadium oxide, ruthenium oxide, tungsten oxide, zinc oxide, tin oxide, iron oxide, molybdenum oxide and the like can be used, and molybdenum oxide is particularly preferable.
  • an organic material hexacyanoazatriphenylene or a derivative thereof can be used.
  • the light emitting layer 6 is a layer containing a compound having a function of transporting injected holes and electrons and a function of generating excitons by recombination of holes and electrons.
  • the compound represented by the general formula (1) according to the present embodiment is preferably included in the light emitting layer 6, and more preferably included in the light emitting dopant.
  • An organic electroluminescent element provided with the light emitting layer 6 containing such a material exhibits blue light emission with a long lifetime and high color purity as compared with a conventional organic electroluminescent element.
  • the content with respect to the host material is preferably 0.01 to 20 wt%, and more preferably 0.1 to 15 wt%.
  • Examples of the host material that forms the light emitting layer 6 together with the light emitting dopant containing the compound of the general formula (1) include organic metal complexes such as tris (8-quinolinolato) aluminum, carbonization such as naphthalene, anthracene, naphthacene, pyrene, and perylene.
  • organic metal complexes such as tris (8-quinolinolato) aluminum, carbonization such as naphthalene, anthracene, naphthacene, pyrene, and perylene.
  • heterocyclic derivatives such as carbazole, thiophene, and furan, and triarylamine derivatives can be used.
  • anthracene derivative and the pyrene derivative used as the light emitting layer host material include compounds represented by the following formulas (III-1) to (III-32).
  • the light emitting layer 6 may contain other compounds such as a host material and a dopant. By mixing other compounds, carrier transport can be adjusted, and by mixing fluorescent dyes, the emission color can be converted and used.
  • the compound that regulates carrier transport include metal complex compounds having 8-quinolinol or a derivative thereof such as tris (8-quinolinolato) aluminum as a ligand, quinoxaline derivatives, pyridine derivatives, pyrimidine derivatives, imidazopyridine derivatives, Electron transporting compounds such as imidazopyrimidine derivatives and phenanthroline derivatives, hole transporting compounds such as triarylamine derivatives, and the like can be preferably used.
  • the electron transport layer 7 has a function of transporting injected electrons and a function of preventing holes from being injected into the electron transport layer 7 from the light emitting layer 6.
  • the electron transport layer 7 includes, for example, organometallic complexes having an 8-quinolinol or a derivative thereof such as tris (8-quinolinolato) aluminum as a ligand, oxadiazole derivatives, triazole derivatives, triazine derivatives, perylene derivatives, quinoline derivatives, Quinoxaline derivatives, diphenylquinone derivatives, nitro-substituted fluorenone derivatives, thiopyrandioxide derivatives, pyridine derivatives, pyrimidine derivatives, imidazopyridine derivatives, imidazopyrimidine derivatives, heterocyclic compounds such as phenanthroline derivatives, anthracene, pyrene, naphthacene, fluoranthene, acenaphtho It can
  • the electron injection layer 8 has a function of facilitating injection of electrons from the second electrode 9 and a function of improving adhesion with the second electrode 9.
  • the electron injection layer 8 is composed of a metal complex, an oxadiazole derivative, a triazole derivative, a triazine derivative, a quinoline derivative, a quinoxaline derivative, a pyridine derivative having an 8-quinolinol or its derivative such as tris (8-quinolinolato) aluminum as a ligand.
  • Pyrimidine derivatives, imidazole derivatives, imidazopyrimidine derivatives, phenanthroline derivatives and the like can be used.
  • the organic electroluminescence device according to this embodiment can be produced by a known method except that the compound for organic electroluminescence device according to this embodiment is contained.
  • a method for forming each organic layer a vacuum vapor deposition method, an ionization vapor deposition method, a coating method, or the like can be appropriately selected and employed depending on the material constituting the organic layer.
  • the coating method include a spin coating method, various printing methods such as gravure printing, and an ink jet method.
  • the solvent used in this coating method include hydrocarbon solvents such as toluene and xylene, and halogen solvents such as dichloroethane.
  • the compound represented by the general formula (1) according to the present embodiment has high solubility and can be sufficiently formed by a coating process.
  • spin coating a thin film with a thickness of about 50 nm to 200 nm can be formed by using a solution having a concentration of about 1 to 3%.
  • Example 1 An ITO transparent electrode having a thickness of 100 nm was formed on a glass substrate by RF sputtering and patterned. This glass substrate with an ITO transparent electrode was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol, and then pulled up from boiling ethanol and dried. The surface of the transparent electrode was washed with UV / O 3 and then fixed to a substrate holder of a vacuum evaporation apparatus, and the inside of the layer was decompressed to 1 ⁇ 10 ⁇ 4 Pa or less.
  • dipyrazino [2,3-f: 2 ′, 3′-h] quinoxaline-2,3,6,7,10,11-hexacarbonitrile (21) having the following structure was obtained.
  • Vapor deposition was performed at a deposition rate of 0.1 nm / sec to a thickness of 5 nm to form a hole injection layer.
  • N, N, N ′, N′-tetrakis (3-biphenylyl) -1,1′-biphenyl-4,4′-diamine (22) having the following structure was deposited at a deposition rate.
  • Vapor deposition was performed at a thickness of 80 nm at 0.1 nm / sec to form a hole transport layer.
  • the compound (III-2) of the present embodiment as a host material and the compound (11) of the present embodiment as a dopant at a mass ratio of 95: 5 and an overall deposition rate of 0.
  • a light emitting layer was formed by vapor deposition to a thickness of 40 nm at 1 nm / sec.
  • the compound (III-2) of the present embodiment was deposited to a thickness of 20 nm at a deposition rate of 0.1 nm / sec to form an electron transport layer.
  • 9,10-bis [4- (imidazo [1,2-a] pyridin-2-yl) phenyl] anthracene (23) having the following structure was deposited at a deposition rate of 0.1 nm / The film was successively deposited to a thickness of 10 nm in sec to form an electron injection layer.
  • LiF was deposited at a deposition rate of 0.1 nm / sec to a thickness of 1.2 nm, used as an electron injection electrode, Al as a protective electrode was deposited to a thickness of 100 nm, and finally sealed with glass to produce organic electroluminescence. An element was obtained.
  • Examples 2 to 15 and Comparative Examples 1 to 6 An organic electroluminescent device was produced in the same manner as in Example 1 except that the compounds listed in Table 2 were used in place of the compounds (III-2) and (11). Table 2 shows the half-life, chromaticity (CIEx, CIEy), and luminous efficiency at an initial luminance of 1000 cd / m 2 when these elements are driven at a current density of 10 mA / cm 2 .
  • the compound used for a comparative example has the structure shown below.
  • the organic electroluminescent device using the compound used in the present embodiment as a dopant was compared with the device using Comparative compounds (31) to (35) as the dopant. It was shown that the half life was long and the blue color purity was high.
  • the dopant used in the present embodiment showed higher luminous efficiency when the light emitting layer was formed using an anthracene or pyrene compound having a dibenzo [a, c] fluorene structure as a host material.
  • Example 16 An ITO transparent electrode having a thickness of 100 nm was formed on a glass substrate by RF sputtering and patterned. This glass substrate with an ITO transparent electrode was subjected to ultrasonic cleaning using a neutral detergent, acetone and ethanol, and then pulled up from boiling ethanol and dried. The surface of the transparent electrode was washed with UV / O 3 and then fixed to a substrate holder of a vacuum evaporation apparatus, and the inside of the layer was decompressed to 1 ⁇ 10 ⁇ 4 Pa or less.
  • the compound (III-2) of the present embodiment and molybdenum oxide as an electron acceptor were formed in a volume ratio of 95: 5 and the film thickness was 50 nm at an overall deposition rate of 0.1 nm / sec. Evaporation was performed to form a hole injection layer.
  • the compound (III-2) of the present embodiment was deposited to a thickness of 50 nm at a deposition rate of 0.1 nm / sec to form a hole transport layer.
  • the compound (III-2) of the present embodiment as a host material and the compound (11) of the present embodiment as a dopant at a volume ratio of 95: 5 and an overall deposition rate of 0.1 nm /
  • the film was deposited in a thickness of 40 nm in sec to obtain a light emitting layer.
  • the compound (III-2) of the present embodiment was deposited to a thickness of 20 nm at a deposition rate of 0.1 nm / sec to form an electron transport layer.
  • the compound (23) was successively deposited to a thickness of 10 nm at a deposition rate of 0.1 nm / sec to obtain an electron injection layer.
  • LiF was deposited at a deposition rate of 0.1 nm / sec to a thickness of 1.2 nm, used as an electron injection electrode, Al as a protective electrode was deposited to a thickness of 100 nm, and finally sealed with glass to produce organic electroluminescence. An element was obtained.
  • Example 17 to 27 An organic electroluminescent device was produced in the same manner as in Example 16 except that the compounds listed in Table 3 were used instead of the compounds (III-2) and (11). Table 3 shows the half-life, chromaticity (CIEx, CIEy), and luminous efficiency at an initial luminance of 1000 cd / m 2 when these elements are driven at a current density of 10 mA / cm 2 .
  • the organic electroluminescent devices using the compounds used in Examples 16 to 27 as dopants were compared with the devices using Comparative compounds (31) to (35) as dopants. It was shown that the luminance half-life was long and the blue color purity was high.
  • the dopant used in the present embodiment showed higher luminous efficiency when the light emitting layer was formed using an anthracene or pyrene compound having a dibenzo [a, c] fluorene structure as a host material.
  • the organic electroluminescent device containing the organic electroluminescent device compound of the present invention in the organic thin film layer can realize long-life blue light emission with high color purity.
  • SYMBOLS 1 Organic electroluminescent element concerning this embodiment, 2 ... Substrate, 3 ... 1st electrode, 4 ... Hole injection layer, 5 ... Hole transport layer, 6 ... Light emitting layer, 7 ... Electron transport layer, 8 ... Electron injection Layer, 9 ... second electrode, P ... power source.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Le but de la présente invention est de fournir un élément électroluminescent organique qui a une longue durée de vie et émettant une lumière bleue ayant une pureté de couleur élevée. Un composé de dibenzo [c, g] fluorène comprenant un groupe de substitution spécifique de la présente invention est contenu dans un élément électroluminescent organique, de ce fait il devient possible de fournir un élément électroluminescent organique qui a une longue durée de vie et émettant une lumière bleue ayant une pureté de couleur élevée.
PCT/JP2017/030908 2017-03-28 2017-08-29 Composé pour élément électroluminescent organique et élément électroluminescent organique Ceased WO2018179482A1 (fr)

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CN112608253A (zh) * 2019-10-03 2021-04-06 佳能株式会社 有机化合物、有机发光元件、显示设备、摄像设备、照明设备和移动物体
KR20210040255A (ko) * 2019-10-03 2021-04-13 캐논 가부시끼가이샤 유기 화합물, 유기발광소자, 표시장치, 촬상 장치, 조명 장치 및 이동체
US11964930B2 (en) 2019-11-07 2024-04-23 Canon Kabushiki Kaisha Organic compound and organic light-emitting element
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US12084397B2 (en) 2019-09-05 2024-09-10 Canon Kabushiki Kaisha Organic compound, organic light-emitting element, display apparatus, photoelectric conversion apparatus, electronic apparatus, lighting apparatus, moving object, and exposure light source
CN112608253A (zh) * 2019-10-03 2021-04-06 佳能株式会社 有机化合物、有机发光元件、显示设备、摄像设备、照明设备和移动物体
KR20210040255A (ko) * 2019-10-03 2021-04-13 캐논 가부시끼가이샤 유기 화합물, 유기발광소자, 표시장치, 촬상 장치, 조명 장치 및 이동체
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JP7218322B2 (ja) 2019-10-03 2023-02-06 キヤノン株式会社 有機化合物、有機発光素子、表示装置、撮像装置、照明装置、移動体
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CN112608253B (zh) * 2019-10-03 2024-04-09 佳能株式会社 有机化合物、有机发光元件、显示设备、摄像设备、照明设备和移动物体
KR102834642B1 (ko) 2019-10-03 2025-07-17 캐논 가부시끼가이샤 유기 화합물, 유기발광소자, 표시장치, 촬상 장치, 조명 장치 및 이동체
US11964930B2 (en) 2019-11-07 2024-04-23 Canon Kabushiki Kaisha Organic compound and organic light-emitting element
CN111100072A (zh) * 2019-11-28 2020-05-05 吉林奥来德光电材料股份有限公司 一种有机光电化合物、其合成方法及有机电致发光器件

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