WO2015170671A1 - Dérivé phénylpyridine, élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage - Google Patents

Dérivé phénylpyridine, élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage Download PDF

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WO2015170671A1
WO2015170671A1 PCT/JP2015/063037 JP2015063037W WO2015170671A1 WO 2015170671 A1 WO2015170671 A1 WO 2015170671A1 JP 2015063037 W JP2015063037 W JP 2015063037W WO 2015170671 A1 WO2015170671 A1 WO 2015170671A1
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cathode
anode
formula
light emitting
electron transport
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和田　淳
幸民 水野
榎本　信太郎
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株式会社 東芝
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D213/00—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members
    • C07D213/02—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members
    • C07D213/04—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom
    • C07D213/24—Heterocyclic compounds containing six-membered rings, not condensed with other rings, with one nitrogen atom as the only ring hetero atom and three or more double bonds between ring members or between ring members and non-ring members having three double bonds between ring members or between ring members and non-ring members having no bond between the ring nitrogen atom and a non-ring member or having only hydrogen or carbon atoms directly attached to the ring nitrogen atom with substituted hydrocarbon radicals attached to ring carbon atoms
    • C07D213/36—Radicals substituted by singly-bound nitrogen atoms
    • C07D213/38—Radicals substituted by singly-bound nitrogen atoms having only hydrogen or hydrocarbon radicals attached to the substituent nitrogen atom
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B44/00—Circuit arrangements for operating electroluminescent light sources
    • 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
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
    • Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps
    • Y02B20/30—Semiconductor lamps, e.g. solid state lamps [SSL] light emitting diodes [LED] or organic LED [OLED]

Definitions

  • Embodiments of the present invention relate to a phenylpyridine derivative, an organic electroluminescent element, a lighting device, and a display device.
  • organic electroluminescent devices researches are being conducted to increase luminous efficiency and lifetime. For example, studies have been made to increase the luminous efficiency and lifetime of organic electroluminescent devices by devising electron transport materials. It has been reported that a molecule including a structure in which a plurality of benzene rings having pyridine having electron withdrawing property and ⁇ electrons are bonded is used as an electron transporting material. However, the lifetime of an organic electroluminescent device using such an electron transport material is short.
  • phenylpyridine derivatives organic electroluminescent elements, lighting devices, and display devices that achieve a long service life.
  • the rings A, B, C and D in the formula (1) are pyridine rings, and each of R1 to R11 in the formula (1) is hydrogen, Any one selected from the group consisting of a chain alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group, and the R1 to R11 are the same as or different from each other.
  • a phenylpyridine derivative is any one selected from the group consisting of a chain alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group.
  • FIG. 1 is a diagram illustrating the lifetime characteristics of the organic electroluminescent device according to the first embodiment.
  • FIG. 2 is a graph showing the weight reduction rate of the electron transport material according to the first embodiment.
  • FIG. 3 is a diagram illustrating the lifetime characteristics of the organic electroluminescent device according to the second embodiment.
  • FIG. 4 is a graph showing the weight reduction rate of the electron transport material according to the second embodiment.
  • FIG. 5 is a cross-sectional view showing an organic electroluminescent element according to the second embodiment.
  • FIG. 6 is a cross-sectional view illustrating an illumination apparatus according to the third embodiment.
  • FIG. 7 is a schematic view showing a display device according to the fourth embodiment.
  • the electron transport material according to the first embodiment will be described.
  • the electron transport material has an electron transport property.
  • the electron transport material in this embodiment is represented by the following formula (1).
  • One molecule of the electron transport material represented by the above formula (1) has seven benzene rings and four pyridine rings A, B, C, and D.
  • Each of the pyridine rings A, B, C, and D has a carbon atom at a position where each of the pyridine rings A, B, C, and D is bonded to the benzene ring.
  • each pyridine ring A, B, C and D is bonded to a benzene ring at the 3 position.
  • each pyridine ring is bonded to a benzene ring at the 2-position.
  • Each pyridine ring A, B, C and D may be bonded to the benzene ring at a different position.
  • each of R1 to R11 is any one selected from the group consisting of hydrogen, a linear alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group.
  • the number of carbons contained in each of a linear alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group is 6 or less.
  • R1 to R11 may be the same as each other or different from each other.
  • Hammett's substituent constant is positive. Therefore, in the embodiment, the “electron-withdrawing heteroaryl group” is, for example, “a heteroaryl group having a positive Hammett substituent constant”.
  • the electron transport material represented by the above formula (1) realizes a long life.
  • Examples of the formula (1) include an electron transport material represented by the following formula (2).
  • the carbon atom contained in the six-membered ring may or may not have a substituent.
  • the carbon atom contained in the six-membered ring may or may not have a substituent.
  • each of R1 to R11 is hydrogen, a linear alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group (eg, a heteroaryl group having a positive Hammett substituent constant) Or any one selected from the group consisting of:
  • the number of carbons contained in each of a linear alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group is 6 or less.
  • R1 to R11 may be the same as each other or different from each other.
  • formula (2) examples include an electron transport material represented by the following formula (3).
  • the carbon atom contained in the six-membered ring may or may not have a substituent.
  • the carbon atom contained in the six-membered ring may or may not have a substituent.
  • each of R1 to R11 is hydrogen, a linear alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group (eg, a heteroaryl group having a positive Hammett substituent constant) Or any one selected from the group consisting of:
  • the number of carbons contained in each of a linear alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group is 6 or less.
  • R1 to R11 may be the same as each other or different from each other.
  • Another example of the above formula (1) is an electron transport material represented by the following formula (4).
  • the carbon atom contained in the six-membered ring may or may not have a substituent.
  • the carbon atom contained in the six-membered ring may or may not have a substituent.
  • each of R1 to R11 is hydrogen, a linear alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group (eg, a heteroaryl group having a positive Hammett substituent constant) Or any one selected from the group consisting of:
  • the number of carbons contained in each of the linear alkyl group, the branched alkyl group, the aryl group, and the electron withdrawing heteroaryl group is 6 or less.
  • R1 to R11 may be the same as each other or different from each other.
  • formula (4) examples include an electron transport material represented by the following formula (5).
  • the carbon atom contained in the six-membered ring may or may not have a substituent.
  • the carbon atom contained in the six-membered ring may or may not have a substituent.
  • each of R1 to R11 is hydrogen, a linear alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group (eg, a heteroaryl group having a positive Hammett substituent constant) Or any one selected from the group consisting of:
  • the number of carbons contained in each of a linear alkyl group, a branched alkyl group, an aryl group, and an electron-withdrawing heteroaryl group is 6 or less.
  • R1 to R11 may be the same as each other or different from each other.
  • the electron transport material represented by the formula (1) In the electron transport material represented by the formula (1), a conjugated system spreads in a structure including seven benzene rings and four pyridine rings. For this reason, the bond between benzene rings and the bond between the benzene ring and the pyridine ring are difficult to cut. Therefore, the electron transport material represented by the formula (1) is hardly decomposed and has high stability. Therefore, the organic electroluminescent element containing the electron transport material represented by the formula (1) as the electron transport layer has a long lifetime.
  • reaction I Under an argon atmosphere, 4-pyridineboronic acid pinacol ester, 1-bromo-3-iodobenzene, Pd (PPh 3 ) 4 , and cesium carbonate were added to the dioxane solution and reacted at 85 ° C. After allowing to cool, toluene and water were added to the reaction solution, liquid separation was performed, and the organic layer was concentrated to obtain a crude product. The resulting crude product was purified with a silica gel column.
  • Reaction II Under an argon atmosphere, the product of Reaction I, bispinacolatoboron, Pd (dppf) Cl 2 , and potassium acetate were added to the DMAc solution and reacted at 80 ° C. After allowing to cool, ethyl acetate and water were added to the reaction solution, and the organic layer was separated to obtain a crude product. The resulting crude product was purified with a silica gel column.
  • Reaction III Under an argon atmosphere, the product of Reaction II, tribromobenzene, Pd (PPh 3 ) 4 , and cesium carbonate were added to the dioxane solution and reacted at 85 ° C. After allowing to cool, toluene and water were added to the reaction solution for liquid separation, and the organic layer was concentrated to obtain a crude product. The resulting crude product was purified with a silica gel column.
  • Reaction IV Under an argon atmosphere, the product of Reaction III, 1,4-phenylenediboronic acid, Pd (PPh 3 ) 4 , and cesium carbonate were added to the dioxane solution and reacted at 85 ° C. After allowing to cool, the precipitated crystals were washed with water, acetone, and DMF. Then, sublimation purification was performed to obtain the target compound Tp4PyPhTP (phenylpyridine derivative) represented by the formula (3).
  • Tp4PyPhTP phenylpyridine derivative
  • organic electroluminescent element containing the synthesized compound represented by formula (3) (phenylpyridine derivative) as an electron transport layer was produced.
  • the layer structure of this element is as follows. In the following, the numbers indicate the thickness of the layers.
  • FIG. 1 is a diagram illustrating the lifetime characteristics of the organic electroluminescent device according to the first embodiment.
  • FIG. 1 shows the evaluation results of the life characteristics of the organic electroluminescent device produced as described above.
  • the lifetime measurement was performed by setting the initial luminance of the organic electroluminescence device to 7000 cd / m 2 , 5000 cd / m 2 , or 3000 cd / m 2 and driving at constant current.
  • the vertical axis in FIG. 1 indicates luminance Int, and the horizontal axis indicates time Tp (h: hour).
  • the acceleration coefficient was calculated from the results of the obtained lifetime characteristics, and the lifetime at an initial luminance of 1000 cd / m 2 was obtained.
  • the acceleration factor was 1.36.
  • the lifetime of the organic electroluminescent element containing the compound represented by the formula (3) as an electron transport layer was 50,000 hours.
  • the organic electroluminescent element containing the compound represented by Formula (3) as an electron transport layer has a long lifetime.
  • the compound represented by the formula (3) is useful as an electron transport material for an organic electroluminescence device.
  • FIG. 2 is a graph showing the weight reduction rate of the electron transport material according to the first embodiment.
  • FIG. 2 shows the measurement results of the weight loss rate for the compound represented by the formula (3). This measurement was performed by raising the temperature of the compound represented by the formula (3) from room temperature to 600 ° C. at a rate of temperature rise of 10 ° C./min. Thermo Mass Photo manufactured by Rigaku Corporation was used as a measuring instrument.
  • the vertical axis in FIG. 2 indicates the weight reduction rate Wd (%), and the horizontal axis indicates the temperature Tm (° C.).
  • the thermal decomposition temperature Td of the compound represented by the formula (3) was 532 ° C. Thus, the thermal decomposition temperature Td of the compound represented by the formula (3) is high.
  • the compound represented by formula (3) is difficult to decompose. Therefore, the organic electroluminescent element containing the compound represented by Formula (3) as an electron transport layer has a long lifetime.
  • reaction I The reaction represented by the following formula (6) was caused.
  • the first compound Com1 was a yellow oil.
  • reaction II The reaction represented by the following formula (7) was caused.
  • the total yield was 15.9 g (GC purity 95%, 53.9 mmol).
  • the yield was 73.9%.
  • the second compound Com2 was a yellow oil.
  • reaction III The reaction represented by the following formula (8) was caused.
  • the precipitated solid was filtered, washed and filtered with pure water, and then washed and filtered with methanol.
  • the obtained wet solid was dried under reduced pressure to obtain 13.9 g of crude crystals.
  • the crude crystals were dissolved by heating under reflux using toluene (930 mL), and left in a refrigerator for about 12 hours.
  • the produced crystals were filtered and washed with a small amount of toluene.
  • Wet crystals were dried under reduced pressure to obtain 11.9 g of crystals.
  • the obtained crystals were dissolved by heating under reflux using toluene (900 mL), and left in a refrigerator for about 12 hours.
  • the produced crystals were filtered and washed with a small amount of toluene.
  • Wet crystals were dried under reduced pressure to obtain 10.7 g of crystals (19.5 mmol).
  • the yield was 47.9%.
  • the crystals were gray.
  • reaction IV The reaction represented by the following formula (9) was caused.
  • reaction solution was extracted with chloroform (1.5 L). Pure water (0.5 L) was added to the aqueous layer, and the mixture was extracted again with chloroform (0.5 L). The organic layer was washed and separated with saturated brine (1 L). The organic layer was dried over sodium sulfate, and the sodium sulfate was removed by filtration and then evaporated to obtain 12.4 g of a solid. The solid was dissolved in chloroform (500 mL), impregnated with silica gel (100 g), and the solvent was evaporated.
  • the yellow crystals were stirred in ethyl acetate (80 mL), and the crystals were filtered and washed twice with ethyl acetate (30 mL).
  • the crystals were dried under reduced pressure to obtain a fourth compound Com4.
  • the yield was 5.80 g (6.88 mmol).
  • the yield was 70.3%.
  • the fourth compound Com4, TpPyPhTP that is, the compound represented by the formula (5) (phenylpyridine derivative) was a colorless crystal.
  • FIG. 3 is a diagram illustrating the lifetime characteristics of the organic electroluminescent device according to the second embodiment.
  • FIG. 3 shows the evaluation results of the life characteristics of the organic electroluminescent device produced as described above. The lifetime measurement was performed by setting the initial luminance of the organic electroluminescence device to 7000 cd / m 2 , 5000 cd / m 2 , or 3000 cd / m 2 and driving at constant current.
  • the vertical axis represents the luminance Int
  • the horizontal axis represents the Tp time (h).
  • the acceleration coefficient was calculated from the results of the obtained lifetime characteristics, and the lifetime at an initial luminance of 1000 cd / m 2 was obtained.
  • the acceleration factor was 1.44.
  • the lifetime of the organic electroluminescent element containing the compound represented by the formula (5) as an electron transport layer was 10,000 hours.
  • the organic electroluminescent element containing the compound represented by Formula (5) as an electron transport layer has a long lifetime.
  • the compound represented by the formula (5) is useful as an electron transport material for an organic electroluminescence device.
  • FIG. 4 is a graph showing the weight reduction rate of the electron transport material according to the second embodiment.
  • FIG. 4 shows the measurement results of the weight loss rate for the compound represented by formula (5). The measurement was performed by heating the compound represented by the formula (5) from room temperature to 600 ° C. at a temperature rising rate of 10 ° C./min. As a measuring instrument, Rigaku's Thermo Mass Photo was used. The vertical axis in FIG. 4 indicates the weight reduction rate Wd (%), and the horizontal axis indicates the temperature Tm (° C.). The thermal decomposition temperature Td of the compound represented by the formula (5) was 533 ° C.
  • the thermal decomposition temperature Td of the compound represented by the formula (5) is high.
  • the compound represented by Formula (5) is difficult to decompose.
  • the compound represented by Formula (5) has a long lifetime. Therefore, the organic electroluminescent element containing the compound represented by Formula (5) as an electron transport layer has a long lifetime.
  • FIG. 5 is a cross-sectional view showing an organic electroluminescent element according to the second embodiment.
  • the organic electroluminescent element 10 includes an anode 12, a cathode 17, a light emitting layer 15 provided between the anode 12 and the cathode 17, and an electron transport layer 16 provided between the light emitting layer 15 and the cathode 17. ,including.
  • the organic electroluminescent element 10 may further include a substrate 11, a hole injection layer 13, and a hole transport layer 14.
  • the anode 12 is provided on the substrate 11.
  • the hole injection layer 13 is provided between the anode 12 and the light emitting layer 15.
  • the hole transport layer 14 is provided between the hole injection layer 13 and the light emitting layer 15.
  • One of the hole injection layer 13 and the hole transport layer 14 may be omitted.
  • an electron injection layer may be provided between the electron transport layer 16 and the cathode 17.
  • the anode 12 injects holes toward the light emitting layer 15.
  • a conductive material is used.
  • a light transmissive conductive material is used.
  • a conductive metal oxide film or a light-transmitting metal thin film can be used.
  • ITO indium oxide, zinc oxide, tin oxide, and indium tin oxide (ITO) which is a composite thereof, or fluorine-doped tin oxide (FTO) is used.
  • gold, platinum, silver or copper is used.
  • an alloy containing gold, platinum, silver and copper can be used.
  • an ITO transparent electrode is preferably used for the anode 12.
  • An organic conductive polymer can also be used for the anode 12.
  • the anode 12 for example, polyaniline and derivatives thereof, or polythiophene and derivatives thereof may be used.
  • the thickness of the ITO film is preferably 30 nm or more and 300 nm or less.
  • the conductivity is lowered and the resistance is increased, which causes the light emission efficiency of the organic electroluminescent element 10 to be lowered.
  • the thickness of the anode 12 is greater than 300 nm, the flexibility of ITO is lowered, and cracks are likely to occur when stress is applied to the anode 12.
  • the anode 12 may be a single layer.
  • the anode 12 may include a plurality of layers that are stacked and have different work functions.
  • the cathode 17 injects electrons toward the light emitting layer 15.
  • a light transmissive conductive material is used for the cathode 17.
  • a conductive metal oxide film, a metal thin film, or the like can be used.
  • a material having a high work function is used as the anode 12
  • a material having a low work function is preferably used for the cathode 17.
  • the work function of the material used for the cathode 17 is lower than the work function of the material used for the anode 12.
  • the material having a low work function include alkali metals and alkaline earth metals. Specific examples of materials having a low work function (materials used for the cathode 17) include Li, In, Al, Ca, Mg, Li, Na, K, Yb, and Cs.
  • the cathode 17 may be a single layer.
  • the cathode 17 may include a plurality of layers that are stacked and have different work functions.
  • An alloy containing two or more metals may be used as the cathode 17. Examples of alloys include lithium-aluminum alloys, lithium-magnesium alloys, lithium-indium alloys, magnesium-silver alloys, magnesium-indium alloys, magnesium-aluminum alloys, indium-silver alloys, and calcium-aluminum alloys. It is done.
  • the thickness of the cathode 17 is preferably 10 nm or more and 300 nm or less. If the thickness of the cathode 17 is thinner than 10 nm, the resistance becomes too large. When the thickness of the cathode 17 is larger than 300 nm, the time for forming the cathode 17 becomes long, damage to other layers occurs, and the performance of the organic electroluminescent element 10 deteriorates.
  • the light emitting layer 15 includes, for example, a host material and a light emitting material.
  • the light emitting layer 15 receives holes from the anode 12 side and receives electrons from the cathode 17 side. In the light emitting layer 15, holes and electrons are recombined.
  • the host material in the light emitting layer 15 is excited by the energy due to this recombination. The energy is transferred from the host material in the excited state to the light emitting dopant, so that the light emitting dopant is in the excited state. Light emission occurs when the luminescent dopant returns to the ground state.
  • a light emitting material (hereinafter referred to as a light emitting dopant) is doped in a host material of an organic material.
  • the thickness of the light emitting layer 15 is preferably 10 nm or more and 100 nm or less.
  • the ratio between the host material and the light emitting dopant is arbitrary.
  • the light emitting layer 15 may further contain an electron transporting material or a hole transporting material. Thereby, for example, the balance of the carriers of holes and electrons in the light emitting layer 15 is optimized, and the light emission efficiency of the organic electroluminescent element 10 is improved.
  • the electron transport layer 16 has a function of receiving electrons from the cathode 17 and transporting the electrons to the light emitting layer 15, for example.
  • the electron transport layer 16 includes a material represented by the formula (1) shown in the first embodiment.
  • the electron transport layer 16 may include a plurality of types of materials represented by the formula (1) shown in the first embodiment.
  • the electron transport layer 16 includes a material represented by the formula (2) or the formula (4) shown in the first embodiment.
  • the electron transport layer 16 includes a material represented by the formula (3) or the formula (5) shown in the first embodiment.
  • the electron transport layer 16 may further include a material other than the material represented by the formula (1).
  • the substrate 11 supports other members, for example. It is preferable that the substrate 11 is hardly changed by heat or an organic solvent.
  • the substrate 11 for example, an inorganic material such as non-alkali glass or quartz glass is used.
  • plastics such as polyethylene, polyethylene terephthalate (PET), polyethylene naphthalate (PEN), polyimide, polyamide, polyamideimide, liquid crystal polymer, and cycloolefin polymer are used.
  • a polymer film is used as the substrate 11.
  • a metal such as stainless steel (SUS) may be used as the substrate 11.
  • a substrate such as silicon may be used as the substrate 11.
  • a light-transmitting substrate for example, a transparent substrate such as glass or synthetic resin. Thereby, light can be extracted through the substrate 11.
  • a light-transmitting substrate for example, a transparent substrate such as glass or synthetic resin.
  • the hole injection layer 13 has a function of receiving holes from the anode 12 and injecting holes into the hole transport layer 14, for example.
  • a polythiophene polymer such as poly (ethylenedioxythiophene): poly (styrenesulfonic acid) (hereinafter referred to as PEDOT: PSS) can be used.
  • PEDOT poly(styrenesulfonic acid)
  • the material used for the hole injection layer 13 is arbitrary.
  • the hole transport layer 14 has a function of receiving holes from the hole injection layer 13 and transporting holes to the light emitting layer 15, for example.
  • a hole transport layer 14 for example, a polymer or a low molecule containing triphenylamine is used.
  • the material used for the hole transport layer 14 is arbitrary.
  • a polymer or a low molecule containing carbazole or the like is used as the light emitting layer 15, for example.
  • the electron injection layer has a function of receiving electrons from the cathode 17 and injecting them into the electron transport layer 16, for example.
  • the electron injection layer for example, CsF or LiF can be used.
  • the material used for the electron injection layer is arbitrary.
  • the anode 12 is disposed between the substrate 11 and the cathode 17.
  • the cathode 17 may be disposed between the substrate 11 and the anode 12.
  • an organic electroluminescent element having a long lifetime and high luminous efficiency can be obtained.
  • FIG. 6 is a cross-sectional view illustrating an illumination apparatus according to the third embodiment.
  • the lighting device 100 includes a substrate 101, a sealing portion 102, an anode 107 provided between the substrate 101 and the sealing portion 102, and a cathode 105 provided between the anode 107 and the sealing portion 102. And an organic layer 106.
  • the organic layer 106 is provided between the anode 107 and the cathode 105.
  • the organic layer 106 includes, for example, a light emitting layer 15 (see FIG. 5) and an electron transport layer 16 (see FIG. 5).
  • the light emitting layer 15 is provided between the anode 107 and the cathode 105.
  • the electron transport layer 16 is provided between the light emitting layer 15 and the cathode 105.
  • the light emitting layer 15 and the electron transport layer 16 are included in the organic layer 106.
  • a drive unit 108 is provided.
  • the drive unit 108 is connected to the anode 107 and the cathode 105.
  • the drive unit 108 controls the potential of the anode 107 and the potential of the cathode 105.
  • the sealing part 102 is arrange
  • the sealing portion 102 is fixed to the substrate 101 using an adhesive 104.
  • an ultraviolet curable adhesive is used for the adhesive 104.
  • the substrate 101 is glass, for example.
  • the sealing part 102 is glass, for example.
  • a desiccant 103 is installed between the sealing unit 102 and the cathode 105.
  • the organic layer 106 includes the light emitting layer 15 and the electron transport layer 16 described in the second embodiment.
  • the electron transport layer 16 includes an electron transport material represented by the formula (1) according to the first embodiment.
  • FIG. 7 is a schematic view showing a display device according to the fourth embodiment.
  • the display device 20 includes a signal line driving circuit 22, a control line driving circuit 23, an organic electroluminescence element 25 connected to the signal line driving circuit 22 and the control line driving circuit 23, a signal line driving circuit 22 and a control line. And a controller 24 connected to the drive circuit 23.
  • the organic electroluminescent element 25 includes an anode 12, a cathode 17, a light emitting layer 15 provided between the anode 12 and the cathode 17, and a space between the light emitting layer 15 and the cathode 17.
  • an electron transport layer 16 provided.
  • the electron transport layer 16 includes an electron transport material represented by the formula (1) according to the first embodiment.
  • a plurality of control lines CL extending in a first direction (for example, a horizontal direction), a plurality of signal lines DL extending in a second direction (for example, a vertical direction), and a plurality of Pixel 21.
  • the second direction intersects the first direction.
  • Pixels 21 are arranged at locations where the control lines CL and the signal lines DL intersect.
  • the plurality of pixels 21 are arranged in a matrix.
  • the pixel 21 includes an organic electroluminescent element 25 and a thin film transistor (TFT) 26 connected to the organic electroluminescent element 25.
  • One terminal of the TFT 26 is connected to the control line CL.
  • the other terminal of the TFT 26 is connected to the signal line DL.
  • the signal line DL is connected to the signal line driving circuit 22.
  • the control line CL is connected to the control line drive circuit 23.
  • the signal line drive circuit 22 and the control line drive circuit 23 are controlled by a controller 24.
  • a display device having a long lifetime and high luminous efficiency can be obtained.
  • a phenylpyridine derivative an organic electroluminescent element, an illumination device, and a display device that provide a long lifetime are provided.
  • phenylpyridine derivatives and organic electroluminescence that can be implemented by those skilled in the art based on the above-described phenylpyridine derivatives, organic electroluminescent elements, lighting devices, and display devices as embodiments of the present invention.
  • An element, a lighting device, and a display device also belong to the scope of the present invention as long as they include the gist of the present invention.

Abstract

La présente invention concerne un dérivé phénylpyridine représenté par la formule (1) [formule chimique 1]. Dans la formule (1), les cycles A, B, C et D sont des cycles pyridine, les R1 à R11 dans la formule (1) sont chacun choisis dans le groupe constitué par des atomes d'hydrogène, des groupes alkyle à chaîne droite, des groupes alkyle à chaîne ramifiée, des groupes aryle et des groupes hétéroaryle attracteurs d'électrons, et les R1 à R11 peuvent être identiques ou différents les uns des autres.
PCT/JP2015/063037 2014-05-09 2015-04-30 Dérivé phénylpyridine, élément électroluminescent organique, dispositif d'éclairage et dispositif d'affichage WO2015170671A1 (fr)

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