WO2012108388A1 - ビスカルバゾール誘導体及びそれを用いた有機エレクトロルミネッセンス素子 - Google Patents
ビスカルバゾール誘導体及びそれを用いた有機エレクトロルミネッセンス素子 Download PDFInfo
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- WO2012108388A1 WO2012108388A1 PCT/JP2012/052639 JP2012052639W WO2012108388A1 WO 2012108388 A1 WO2012108388 A1 WO 2012108388A1 JP 2012052639 W JP2012052639 W JP 2012052639W WO 2012108388 A1 WO2012108388 A1 WO 2012108388A1
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- 125000004434 sulfur atom Chemical group 0.000 description 1
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- 125000001544 thienyl group Chemical group 0.000 description 1
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- XOLBLPGZBRYERU-UHFFFAOYSA-N tin dioxide Chemical compound O=[Sn]=O XOLBLPGZBRYERU-UHFFFAOYSA-N 0.000 description 1
- 229910001887 tin oxide Inorganic materials 0.000 description 1
- 150000003852 triazoles Chemical group 0.000 description 1
- 125000002306 tributylsilyl group Chemical group C(CCC)[Si](CCCC)(CCCC)* 0.000 description 1
- 125000002023 trifluoromethyl group Chemical group FC(F)(F)* 0.000 description 1
- 125000000026 trimethylsilyl group Chemical group [H]C([H])([H])[Si]([*])(C([H])([H])[H])C([H])([H])[H] 0.000 description 1
- ODHXBMXNKOYIBV-UHFFFAOYSA-N triphenylamine Chemical compound C1=CC=CC=C1N(C=1C=CC=CC=1)C1=CC=CC=C1 ODHXBMXNKOYIBV-UHFFFAOYSA-N 0.000 description 1
- PXFBSZZEOWJJNL-UHFFFAOYSA-N triphenylen-2-ylboronic acid Chemical compound C1=CC=C2C3=CC(B(O)O)=CC=C3C3=CC=CC=C3C2=C1 PXFBSZZEOWJJNL-UHFFFAOYSA-N 0.000 description 1
- 229910000404 tripotassium phosphate Inorganic materials 0.000 description 1
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- NHDIQVFFNDKAQU-UHFFFAOYSA-N tripropan-2-yl borate Chemical compound CC(C)OB(OC(C)C)OC(C)C NHDIQVFFNDKAQU-UHFFFAOYSA-N 0.000 description 1
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Definitions
- the present invention relates to a biscarbazole derivative and an organic electroluminescence device using the biscarbazole derivative, and particularly to an organic electroluminescence device having high emission efficiency and a long lifetime and a biscarbazole derivative that realizes the organic electroluminescence device.
- This light-emitting element is characterized by thin light emission with high luminance under a low driving voltage and multicolor light emission by selecting a light-emitting material.
- an organic electroluminescence element (hereinafter referred to as an organic EL element)
- holes from the anode and electrons from the cathode are injected into the light emitting layer.
- the injected holes and electrons are recombined to form excitons.
- singlet excitons and triplet excitons are generated at a ratio of 25%: 75% according to the statistical rule of electron spin.
- the fluorescence type uses light emitted from singlet excitons, and therefore the internal quantum efficiency of the organic EL element is said to be limited to 25%.
- the internal quantum efficiency can be increased to 100% when intersystem crossing is efficiently performed from singlet excitons.
- an optimal element design has been made according to a light emission mechanism of a fluorescent type and a phosphorescent type.
- phosphorescent organic EL elements cannot obtain high-performance elements by simple diversion of fluorescent element technology because of their light emission characteristics. The reason is generally considered as follows. First, since phosphorescence emission is emission using triplet excitons, the energy gap of the compound used in the light emitting layer must be large.
- the value of the energy gap (hereinafter also referred to as singlet energy) of a compound usually refers to the triplet energy of the compound (in the present invention, the energy difference between the lowest excited triplet state and the ground state). This is because it is larger than the value of).
- a host material having a triplet energy larger than the triplet energy of the phosphorescent dopant material must be used for the light emitting layer. Don't be.
- an electron transport layer and a hole transport layer adjacent to the light emitting layer are provided, and a compound having a triplet energy higher than that of the phosphorescent dopant material must be used for the electron transport layer and the hole transport layer.
- a compound having a larger energy gap than the compound used for the fluorescent organic EL element is used for the phosphorescent organic EL element.
- the drive voltage of the entire element increases.
- hydrocarbon compounds with high oxidation resistance and reduction resistance which are useful in fluorescent elements, have a large energy gap due to a large spread of ⁇ electron clouds. Therefore, in the phosphorescent organic EL element, such a hydrocarbon compound is difficult to select, and an organic compound containing a hetero atom such as oxygen or nitrogen is selected. As a result, the phosphorescent organic EL element is There is a problem that the lifetime is shorter than that of a fluorescent organic EL element. Furthermore, the fact that the exciton relaxation rate of the triplet exciton of the phosphorescent dopant material is much longer than that of the singlet exciton also greatly affects the device performance.
- a dopant material a fluorescent (singlet light emission) material is generally used in the past, but a phosphorescent (triplet light emission) material has been used in order to improve the light emission efficiency. Attempts have been made and a group at Princeton University has shown that the luminous efficiency is significantly higher than conventional fluorescent materials (see Non-Patent Document 1).
- a phosphorescent dopant material a technique using a metal complex having iridium, osmium, rhodium, palladium, platinum or the like as a central metal is disclosed (see Patent Documents 2 to 4).
- Patent Document 7 a technique for using a biscarbazole derivative as a hole transport material of a fluorescent element is disclosed (Patent Document 7).
- Patent Document 8 describes an example of a biscarbazole derivative as a host material combined with a specific metal complex dopant.
- Patent Document 9 describes the use of a biscarbazole derivative as a host material.
- Patent Document 9 a substituent that improves the carrier transportability of the host material, such as an amino substituent-containing phenyl group, naphthyl group, or fluorenyl group, is introduced at the N-position of the carbazole structure. As a result, the voltage of the light emitting device is reduced, but the device lifetime is not specifically known.
- the present invention has been made under such circumstances, and an object of the present invention is to provide an organic electroluminescence device having high luminous efficiency and a long lifetime, and a biscarbazole derivative for realizing the organic electroluminescence device.
- a biscarbazole derivative represented by the following formula (1).
- a 1 and A 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
- Y 1 to Y 16 each independently represent C (R) or a nitrogen atom, and each R independently represents a hydrogen atom, a substituent, or a bond bonded to a carbazole skeleton.
- L 1 and L 2 are each independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted 2 to 30 ring carbon atom having 2 to 30 carbon atoms.
- a valent aromatic heterocyclic group is independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted 2 to 30 ring carbon atom having 2 to 30 carbon atoms.
- a 1 , A 2 and R is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted group Benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or unsubstituted picenyl group, substituted or unsubstituted benzo [b] Fluoranthenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted binaphthyl group, substituted or unsubstituted dibenzophenanthrenyl group, substituted or unsubstituted fluoranthen
- Y 1 to Y 16 are all C (R), R is hydrogen, Y 6 and Y 11 are bonded by a single bond, L 1 and L 2 are a single bond, and A 1 is a phenanthrenyl group. In this case, A 2 is a phenyl group, a biphenylyl group or a naphthyl group.
- Y 1 to Y 16 are all C (R), R is hydrogen, Y 6 and Y 11 are bonded by a single bond, L 1 and L 2 are a single bond, and A 1 is a naphthyl group. In this case, A 1 and A 2 are different from each other.
- At least one of A 1 and A 2 is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, A substituted or unsubstituted benzotriphenylenyl group, a substituted or unsubstituted dibenzotriphenylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted picenyl group, or a substituted or unsubstituted A substituted benzo [b] fluoranthenyl group, a substituted or unsubstituted phenanthrenyl group, a substituted or unsubstituted binaphthyl group, a substituted or un
- the biscarbazole derivative according to any one of [1] to [5], wherein L 1 and L 2 are divalent linking groups.
- the A 1 is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted benzotriphenylenyl group, a substituted Or an unsubstituted dibenzotriphenylenyl group, a substituted or unsubstituted chrysenyl group, a substituted or unsubstituted benzochrysenyl group, a substituted or unsubstituted picenyl group, or a substituted or unsubstituted benzo [b] fluoranthenyl group, substituted Or an unsubstituted phenanthrenyl group, a substituted or unsubstitute
- one of A 1a and A 2a is a group represented by the following formula (a), and the other is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzophenanthrene.
- Nyl group substituted or unsubstituted picenyl group, substituted or unsubstituted benzo
- fluoranthenyl group substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted binaphthyl group, substituted or unsubstituted dibenzophenanthrene
- Y 1a to Y 16a each independently represent C (R) or a nitrogen atom, and each R independently represents a bond bonded to a hydrogen atom, a substituent or a carbazole skeleton.
- L 1a and L 2a are each independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted 2 to 30 ring carbon atom having 2 to 30 carbon atoms.
- Y 21 to Y 25 each independently represent C (R a ) or a nitrogen atom, and each R a independently represents a hydrogen atom or a substituent.
- a plurality of organic thin film layers including a light emitting layer are provided between the cathode and the anode, and at least one of the organic thin film layers includes the biscarbazole derivative according to any one of [1] to [9] Organic electroluminescence device.
- Organic electroluminescence having a plurality of organic thin film layers including a light emitting layer between a cathode and an anode, wherein at least one of the organic thin film layers includes a biscarbazole derivative represented by the following formula (10) element.
- one of A 1 ′ and A 2 ′ represents a substituted or unsubstituted fluorenyl group, and the other represents a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
- Y 1 ′ to Y 16 ′ each independently represent C (R ′) or a nitrogen atom, and R ′ each independently represents a bond bonded to a hydrogen atom, a substituent or a carbazole skeleton.
- L 1 ′ and L 2 ′ are each independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring carbon number 2 to 30 Of the divalent aromatic heterocyclic group.
- the luminescent layer includes the biscarbazole derivative as a host material.
- the light emitting layer contains a phosphorescent material.
- the light-emitting layer includes a host material and a phosphorescent material, and the phosphorescent material is an orthometalated complex of metal atoms selected from iridium (Ir), osmium (Os), and platinum (Pt).
- the organic electroluminescent element of description [15] The organic electroluminescence device according to [14], which has an electron injection layer between the cathode and the light emitting layer, and the electron injection layer contains a nitrogen-containing ring derivative. [16] The organic electroluminescence device according to [15], which has an electron transport layer between the cathode and the light emitting layer, and the electron transport layer contains the biscarbazole derivative.
- the organic electroluminescence device according to [16] which has a hole transport layer between the anode and the light emitting layer, and the hole transport layer contains the biscarbazole derivative.
- An illumination device comprising the organic electroluminescence element according to any one of [10] to [18].
- a display device comprising the organic electroluminescence element according to any one of [10] to [19].
- an organic electroluminescence device having high luminous efficiency and a long lifetime, and a biscarbazole derivative for realizing the organic electroluminescence device.
- the organic EL element 1 includes a transparent substrate 2, an anode 3, a cathode 4, and an organic thin film layer 10 disposed between the anode 3 and the cathode 4.
- the organic thin film layer 10 has a phosphorescent light emitting layer 5 containing a phosphorescent host as a host material and a phosphorescent dopant as a phosphorescent material, and a phosphorescent layer such as a hole injection / transport layer 6 between the phosphorescent light emitting layer 5 and the anode 3.
- An electron injection / transport layer 7 or the like may be provided between the light emitting layer 5 and the cathode 4.
- an electron barrier layer may be provided on the phosphorescent light emitting layer 5 on the anode 3 side, and a hole barrier layer may be provided on the phosphorescent light emitting layer 5 on the cathode 4 side.
- the organic EL device of the present invention may be a fluorescent or phosphorescent monochromatic light emitting device, a fluorescent / phosphorescent hybrid white light emitting device, or a simple type having a single light emitting unit. Alternatively, a tandem type having a plurality of light emitting units may be used.
- the “light emitting unit” refers to a minimum unit that includes one or more organic layers, one of which is a light emitting layer, and can emit light by recombination of injected holes and electrons. A typical layer structure of the light emitting unit is shown below.
- A Hole transport layer / light emitting layer (/ electron transport layer)
- B Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer (/ electron transport layer)
- C Hole transport layer / phosphorescent layer / space layer / fluorescent layer (/ electron transport layer)
- D Hole transport layer / first phosphorescent light emitting layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
- E Hole transport layer / first phosphorescent light emitting layer / space layer / second phosphorescent light emitting layer / space layer / fluorescent light emitting layer (/ electron transport layer)
- F Hole transport layer / phosphorescent layer / space layer / first fluorescent layer / second fluorescent layer (/ electron transport layer)
- the following element structure can be mentioned as a typical element structure of a tandem type organic EL element.
- the first light emitting unit and the second light emitting unit for example, the same light emitting unit as that described above can be selected independently. it can.
- the intermediate layer is generally called an intermediate electrode, an intermediate conductive layer, a charge generation layer, an electron extraction layer, a connection layer, or an intermediate insulating layer, and has electrons in the first light emitting unit and holes in the second light emitting unit.
- a known material structure to be supplied can be used.
- the terms fluorescent host and phosphorescent host are referred to as a fluorescent host when combined with a fluorescent dopant, and are referred to as a phosphorescent host when combined with a phosphorescent dopant. It is not limited to fluorescent hosts or phosphorescent hosts.
- the fluorescent host means a material constituting a fluorescent light-emitting layer containing a fluorescent dopant, and does not mean a material that can be used only as a host of the fluorescent light-emitting material.
- a phosphorescent host means a material constituting a phosphorescent light emitting layer containing a phosphorescent dopant, and does not mean a material that can be used only as a host of a phosphorescent material.
- hole injection / transport layer means “at least one of a hole injection layer and a hole transport layer”
- electron injection / transport layer means “electron injection layer” And / or “at least one of the electron transport layers”.
- the organic EL element of the present invention is produced on a translucent substrate.
- the light-transmitting substrate is a substrate that supports the organic EL element, and is preferably a smooth substrate having a light transmittance in the visible region of 400 nm to 700 nm of 50% or more.
- a glass plate, a polymer plate, etc. are mentioned.
- the glass plate include those using soda lime glass, barium / strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, barium borosilicate glass, quartz and the like as raw materials.
- the polymer plate include those using polycarbonate, acrylic, polyethylene terephthalate, polyether sulfide, polysulfone and the like as raw materials.
- the anode of the organic EL element plays a role of injecting holes into the hole injection layer, the hole transport layer, or the light emitting layer, and it is effective to have a work function of 4.5 eV or more.
- Specific examples of the anode material include indium tin oxide alloy (ITO), tin oxide (NESA), indium zinc oxide, gold, silver, platinum, copper, and the like.
- the anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
- the light transmittance in the visible region of the anode be greater than 10%.
- the sheet resistance of the anode is preferably several hundred ⁇ / ⁇ or less.
- the film thickness of the anode depends on the material, but is usually selected in the range of 10 nm to 1 ⁇ m, preferably 10 nm to 200 nm.
- the cathode a material having a small work function is preferable for the purpose of injecting electrons into the electron injection layer, the electron transport layer, or the light emitting layer.
- the cathode material is not particularly limited, and specifically, indium, aluminum, magnesium, magnesium-indium alloy, magnesium-aluminum alloy, aluminum-lithium alloy, aluminum-scandium-lithium alloy, magnesium-silver alloy and the like can be used.
- the cathode can be produced by forming a thin film by a method such as vapor deposition or sputtering.
- the aspect which takes out light emission from a cathode side is also employable.
- the light emitting layer of the organic EL element has the following functions. That is, (1) injection function; a function capable of injecting holes from the anode or hole injection layer when an electric field is applied, and a function of injecting electrons from the cathode or electron injection layer; (2) Transport function; function to move injected charges (electrons and holes) by the force of electric field, (3) Luminescent function; a function to provide a field for recombination of electrons and holes and connect this to light emission, There is.
- a known method such as an evaporation method, a spin coating method, or an LB method can be applied.
- the light emitting layer is preferably a molecular deposited film.
- the molecular deposition film is a thin film formed by deposition from a material compound in a gas phase state or a film formed by solidification from a material compound in a solution state or a liquid phase state. Can be distinguished from the thin film (molecular accumulation film) formed by the LB method by the difference in the aggregated structure and the higher order structure and the functional difference resulting therefrom.
- the light emitting layer can also be formed by dissolving a binder such as a resin and a material compound in a solvent to form a solution, and then thinning the solution by a spin coating method or the like.
- the organic EL device of the present invention includes an organic thin film layer composed of one or more layers between a cathode and an anode, and the organic thin film layer has at least one light emitting layer, and at least one of the organic thin film layers.
- the layer contains at least one phosphorescent material and at least one organic electroluminescent element material of the present invention described later.
- at least one of the light emitting layers contains the material for an organic electroluminescence element of the present invention and at least one phosphorescent material.
- the organic EL device of the present invention has a plurality of organic thin film layers including a light emitting layer between a cathode and an anode, and at least one of the organic thin film layers contains a biscarbazole derivative.
- “hydrogen” includes deuterium.
- the biscarbazole derivative of the present invention preferably has only two carbazole structures in the molecule.
- the biscarbazole derivative of the present invention includes a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted benzotriphenylenyl at a specific position.
- a 1 and A 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms.
- Y 1 to Y 16 each independently represent C (R) or a nitrogen atom, and each R independently represents a hydrogen atom, a substituent, or a bond bonded to a carbazole skeleton.
- L 1 and L 2 are each independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted 2 to 30 ring carbon atom having 2 to 30 carbon atoms.
- a 1 , A 2 and R is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted group Benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or unsubstituted picenyl group, substituted or unsubstituted benzo [b] Fluoranthenyl group, substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted binaphthyl group, substituted or unsubstituted dibenzophenanthrenyl group, substituted or unsubstituted fluoranthen
- Y 1 to Y 16 are all C (R), R is hydrogen, Y 6 and Y 11 are bonded by a single bond, L 1 and L 2 are a single bond, and A 1 is a phenanthrenyl group. In this case, A 2 is a phenyl group, a biphenylyl group or a naphthyl group.
- Y 1 to Y 16 are all C (R), R is hydrogen, Y 6 and Y 11 are bonded by a single bond, L 1 and L 2 are a single bond, and A 1 is a naphthyl group. In this case, A 1 and A 2 are different from each other. )
- At least one of Y 1 to Y 4 is C (R), at least one of Y 5 to Y 8 is C (R), and Y At least one of 9 to Y 12 is C (R), and at least one of Y 13 to Y 16 is C (R).
- One of Y 5 to Y 8 is C (R), and one of Y 9 to Y 12 is C (R), and these Rs represent bonds that are bonded to each other.
- R in Formula (1) and (1 ') may mutually be same or different.
- At least one of Y 1a to Y 4a is C (R)
- at least one of Y 5a to Y 8a is C (R)
- at least one of Y 9a to Y 12a One is C (R)
- at least one of Y 13a to Y 16a is C (R)
- One of Y 5a to Y 8a is C (R)
- one of Y 9a to Y 12a is C (R).
- At least one of Y 1 ′ to Y 4 ′ is C (R ′), at least one of Y 5 ′ to Y 8 ′ is C (R ′), and Y 9 At least one of ' to Y 12' is C (R '), and at least one of Y 13' to Y 16 ' is C (R').
- One of Y 5 ′ to Y 8 ′ is C (R ′), and one of Y 9 ′ to Y 12 ′ is C (R ′), and these R ′ are bonded to each other. Represents a bond.
- R 'in Formula (10) may mutually be same or different.
- a 1 , A 2 , Y 1 to Y 16 , L 1 and L 2 are the same as those in the formula (1)).
- a 1 and A 2 are each independently a substituted or unsubstituted aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring having 2 to 30 ring carbon atoms. Represents a substituted aromatic heterocyclic group.
- Y 1 to Y 16 each independently represent C (R) or a nitrogen atom, and each R independently represents a hydrogen atom, a substituent, or a bond bonded to a carbazole skeleton.
- L 1 and L 2 are each independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted 2 to 30 ring carbon atom having 2 to 30 carbon atoms.
- a valent aromatic heterocyclic group is independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted 2 to 30 ring carbon atom having 2 to 30 carbon atoms.
- a 1 , A 2 and R is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted group Benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or unsubstituted picenyl group, or substituted or unsubstituted benzo [b ] Fluoranthenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsubstituted
- Y 1 to Y 16 are all C (R)
- R is hydrogen
- Y 6 and Y 11 are bonded by a single bond
- L 1 and L 2 are a single bond
- a 1 is a phenanthrenyl group.
- a 2 is not a phenanthrenyl group.
- R is not a fluorenyl group
- a 1 is a fluorenyl group
- a 2 is not a phenyl group, a naphthyl group, or a fluorenyl group.
- one of A 1a and A 2a is a group represented by the following formula (a), and the other is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted benzophenanthrene.
- Nyl group substituted or unsubstituted picenyl group, substituted or unsubstituted benzo
- fluoranthenyl group substituted or unsubstituted phenanthrenyl group, substituted or unsubstituted binaphthyl group, substituted or unsubstituted dibenzophenanthrene
- Y 1a to Y 16a each independently represent C (R) or a nitrogen atom, and each R independently represents a bond bonded to a hydrogen atom, a substituent or a carbazole skeleton.
- L 1a and L 2a are each independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted 2 to 30 ring carbon atom having 2 to 30 carbon atoms.
- a valent aromatic heterocyclic group is each independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted 2 to 30 ring carbon atom having 2 to 30 carbon atoms.
- Y 21 to Y 25 each independently represent C (R a ) or a nitrogen atom, and each R a independently represents a hydrogen atom or a substituent.
- the details of A 1a , A 2a , Y 1a to Y 16a , L 1a , L 2a, and R a in formula (1a) and formula (a) are as follows: A 1 , A 2 , Y 1 to The same as Y 16 , L 1 , L 2 and R.
- one of A 1 ′ and A 2 ′ is a substituted or unsubstituted naphthyl group or a substituted or unsubstituted fluorenyl group, and the other is a substituted or unsubstituted group having 6 to 30 ring carbon atoms.
- Y 1 ′ to Y 16 ′ each independently represent C (R ′) or a nitrogen atom, and R ′ each independently represents a bond bonded to a hydrogen atom, a substituent or a carbazole skeleton.
- L 1 ′ and L 2 ′ are each independently a single bond, a substituted or unsubstituted divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms, or a substituted or unsubstituted ring carbon number 2 to 30 Of the divalent aromatic heterocyclic group.
- the details of A 1 ′ , A 2 ′ , L 1 ′ , L 2 ′ , Y 1 ′ to Y 16 ′ and R ′ in the formula (10) are as follows: A 1 , A 2 , L 1 , The same as L 2 , Y 1 to Y 16 and R.
- At least one of A 1 , A 2 and R is a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, substituted or unsubstituted Benzophenanthrenyl group, substituted or unsubstituted benzotriphenylenyl group, substituted or unsubstituted dibenzotriphenylenyl group, substituted or unsubstituted chrysenyl group, substituted or unsubstituted benzochrysenyl group, substituted or unsubstituted Picenyl group, substituted or unsubstituted benzo [b] fluoranthenyl group, substituted or unsubstituted benzofuranyl group, substituted or unsubstituted dibenzofuranyl group, substituted or unsubstituted benzothiophenyl group, substituted or unsub
- a 1 and A 2 are each independently a substituted or unsubstituted fluoranthenyl group, a substituted or unsubstituted triphenylenyl group, substituted or unsubstituted It is preferably a substituted benzotriphenylenyl group, a substituted or unsubstituted benzophenanthrenyl group, a substituted or unsubstituted dibenzofuranyl group, or a substituted or unsubstituted dibenzothiophenyl group.
- the substituted or unsubstituted phenyl group represented by any of A 1 , A 2 and R is preferably a phenyl group substituted with an aromatic hydrocarbon group having 10 to 30 carbon atoms, and particularly preferably a naphthylphenyl group. .
- a 1 and A 2 in the formulas (1) to (4) and (1 ′) is a group represented by the formula (a)
- a host material used together with a green light-emitting dopant Particularly preferred.
- Y 21 and / or Y 25 preferably represents a nitrogen atom, and more preferably Y 22 and Y 24 represent C (R a ).
- substituents represented by A 1 and A 2 in the general formulas (1) to (4) and (1 ′) and the substituents represented by R and R a include a fluorine atom, a cyano group, and a substituent. Or an unsubstituted linear, branched or cyclic alkyl group having 1 to 20 carbon atoms, a linear, branched or cyclic alkylene group having 1 to 20 carbon atoms, and a linear chain having 1 to 20 carbon atoms.
- Branched or cyclic divalent unsaturated hydrocarbon group substituted or unsubstituted linear, branched or cyclic alkoxy group having 1 to 20 carbon atoms, substituted or unsubstituted carbon atoms of 1 to 20 straight-chain, branched-chain or cyclic haloalkyl groups, substituted or unsubstituted straight-chain, branched-chain or cyclic haloalkoxy groups, substituted or unsubstituted 1-10 carbon atoms
- substituents may be plural, and when plural, they may be the same as or different from each
- linear, branched or cyclic alkyl group having 1 to 20 carbon atoms examples include, for example, methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, t -Butyl, n-pentyl, n-hexyl, n-heptyl, n-octyl, n-nonyl, n-decyl, n-undecyl, n-dodecyl, n-tridecyl, n -Tetradecyl group, n-pentadecyl group, n-hexadecyl group, n-heptadecyl group, n-octadecyl group, neopentyl group, 1-methylpentyl group, 2-methylpentyl group, 1-pentylhexyl group
- Examples of the linear, branched or cyclic alkylene group having 1 to 20 carbon atoms include an ethylene group, a propylene group, and a butylene group.
- Examples of the linear, branched or cyclic divalent unsaturated hydrocarbon group having 1 to 20 carbon atoms include a 1,3-butadiene-1,4-diyl group.
- Examples of the linear, branched or cyclic alkylsilyl group having 1 to 10 carbon atoms include a trimethylsilyl group, a triethylsilyl group, a tributylsilyl group, a dimethylethylsilyl group, a dimethylisopropylsilyl group, and a dimethylpropylsilyl group.
- Examples of the arylsilyl group having 6 to 30 carbon atoms include a phenyldimethylsilyl group, a diphenylmethylsilyl group, a diphenyl tertiary butylsilyl group, and a triphenylsilyl group.
- halogen atoms include fluorine atoms.
- Examples of the aromatic heterocyclic group having 2 to 30 ring carbon atoms include a non-condensed aromatic heterocyclic ring and a condensed aromatic heterocyclic ring, and more specifically, a pyrrolyl group, a pyrazinyl group, a pyridinyl group, an indolyl group.
- Examples of the aromatic hydrocarbon group having 6 to 30 ring carbon atoms include a non-condensed aromatic hydrocarbon group and a condensed aromatic hydrocarbon group. More specifically, a phenyl group, a naphthyl group, a phenanthryl group, Biphenyl group, terphenyl group, quarterphenyl group, fluoranthenyl group, triphenylenyl group, phenanthrenyl group, 9,9-dimethylfluorenyl group, benzo [c] phenanthrenyl group, benzo [a] triphenylenyl group, naphtho [1, 2-c] phenanthrenyl group, naphtho [1,2-a] triphenylenyl group, dibenzo [a, c] triphenylenyl group, benzo [b] fluoranthenyl group, and the like.
- the divalent linking group represented by L 1 and L 2 in the general formulas (1) to (4) and (1 ′) is a substituted or unsubstituted divalent fragrance having 6 to 30 ring carbon atoms.
- Specific examples of the divalent aromatic hydrocarbon group having 6 to 30 ring carbon atoms include those having a divalent group as the aromatic hydrocarbon group having 6 to 30 ring carbon atoms described above. Can be mentioned.
- specific examples of the divalent aromatic heterocyclic group having 2 to 30 ring carbon atoms include those mentioned above as the aromatic heterocyclic group having 2 to 30 ring carbon atoms. Things.
- Y 1 to Y 16 are preferably all C (R).
- the number of substituents represented by R is preferably 0 to 2 in each of Y 1 to Y 8 and Y 9 to Y 16. , 0 or 1 is more preferable.
- biscarbazole derivatives of the present invention represented by the general formulas (1) to (4), (1 ′) and (10) include the following compounds.
- D represents deuterium.
- the light emitting layer preferably contains the biscarbazole derivative of the present invention.
- the organic EL device of the present invention preferably has a hole transport layer (hole injection layer), and the hole transport layer (hole injection layer) preferably contains the biscarbazole derivative of the present invention.
- the phosphorescent material contains a metal complex, and the metal complex has a metal atom selected from Ir, Pt, Os, Au, Cu, Re, and Ru, and a ligand. preferable.
- the ligand preferably has an ortho metal bond.
- a compound containing a metal atom selected from Ir, Os and Pt is preferable in that the phosphorescent quantum yield is high and the external quantum efficiency of the light emitting device can be further improved, and an iridium complex, an osmium complex, platinum Metal complexes such as complexes are more preferred, with iridium complexes and platinum complexes being more preferred, and orthometalated iridium complexes being most preferred. Specific examples of preferable metal complexes are shown below.
- At least one of the phosphorescent materials included in the light emitting layer has a maximum emission wavelength of 450 nm or more and 750 nm or less.
- the maximum value is 450 nm or more and 495 nm or less, 495 nm or more and 590 nm or less, and 590 nm or more and 750 nm or less.
- a highly efficient organic EL device can be obtained by forming a light emitting layer by doping a phosphorescent material (phosphorescent dopant) having such an emission wavelength into a specific host material used in the present invention.
- the organic EL device of the present invention preferably has a reducing dopant in the interface region between the cathode and the organic thin film layer. According to such a configuration, it is possible to improve the light emission luminance and extend the life of the organic EL element.
- the reducing dopant was selected from alkali metals, alkali metal complexes, alkali metal compounds, alkaline earth metals, alkaline earth metal complexes, alkaline earth metal compounds, rare earth metals, rare earth metal complexes, rare earth metal compounds, and the like. There is at least one kind.
- alkali metal examples include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), Cs (work function: 1.95 eV), and the like.
- a function of 2.9 eV or less is particularly preferable. Of these, K, Rb, and Cs are preferred, Rb and Cs are more preferred, and Cs is most preferred.
- alkaline earth metals include Ca (work function: 2.9 eV), Sr (work function: 2.0 eV to 2.5 eV), Ba (work function: 2.52 eV), and the like. The thing below 9 eV is especially preferable.
- rare earth metals include Sc, Y, Ce, Tb, Yb, and the like, and those having a work function of 2.9 eV or less are particularly preferable.
- preferred metals are particularly high in reducing ability, and by adding a relatively small amount to the electron injection region, it is possible to improve the light emission luminance and extend the life of the organic EL element.
- alkali metal compound examples include alkali oxides such as Li 2 O, Cs 2 O, and K 2 O, and alkali halides such as LiF, NaF, CsF, and KF, and LiF, Li 2 O, and NaF are preferable.
- alkaline earth metal compound examples include BaO, SrO, CaO, and Ba x Sr 1-x O (0 ⁇ x ⁇ 1), Ba x Ca 1-x O (0 ⁇ x ⁇ 1) mixed with these. BaO, SrO, and CaO are preferable.
- the rare earth metal compound, YbF 3, ScF 3, ScO 3, Y 2 O 3, Ce 2 O 3, GdF 3, TbF 3 and the like, YbF 3, ScF 3, TbF 3 are preferable.
- the alkali metal complex, alkaline earth metal complex, and rare earth metal complex are not particularly limited as long as each metal ion contains at least one of an alkali metal ion, an alkaline earth metal ion, and a rare earth metal ion.
- the ligands include quinolinol, benzoquinolinol, acridinol, phenanthridinol, hydroxyphenyloxazole, hydroxyphenylthiazole, hydroxydiaryloxadiazole, hydroxydiarylthiadiazole, hydroxyphenylpyridine, hydroxyphenylbenzimidazole, hydroxybenzotriazole, Hydroxyfulborane, bipyridyl, phenanthroline, phthalocyanine, porphyrin, cyclopentadiene, ⁇ -diketones, azomethines, and derivatives thereof are preferred, but not limited thereto.
- the addition form of the reducing dopant it is preferable to form a layered or island-like shape in the interface region.
- a formation method a method in which a reducing dopant is deposited in the organic material by simultaneously depositing a light emitting material forming an interface region or an organic material that is an electron injection material while depositing a reducing dopant by a resistance heating vapor deposition method is preferable.
- the reducing dopant is vapor-deposited alone by resistance heating vapor deposition, preferably the layer thickness is 0. It is formed at 1 nm to 15 nm.
- the reducing dopant is vapor-deposited by resistance heating vapor deposition alone, preferably the thickness of the island The film is formed at 0.05 nm to 1 nm.
- the electron injection layer or the electron transport layer is a layer that assists the injection of electrons into the light emitting layer, and has a high electron mobility.
- the electron injection layer is provided to adjust the energy level, for example, to alleviate a sudden change in the energy level.
- the organic EL device of the present invention preferably has an electron injection layer between the light emitting layer and the cathode, and the electron injection layer preferably contains a nitrogen-containing ring derivative as a main component.
- the electron injection layer may be a layer that functions as an electron transport layer. “As a main component” means that the electron injection layer contains 50% by mass or more of a nitrogen-containing ring derivative.
- an aromatic heterocyclic compound containing at least one hetero atom in the molecule is preferably used, and a nitrogen-containing ring derivative is particularly preferable.
- the nitrogen-containing ring derivative is preferably an aromatic ring having a nitrogen-containing 6-membered ring or 5-membered ring skeleton, or a condensed aromatic ring compound having a nitrogen-containing 6-membered ring or 5-membered ring skeleton.
- a nitrogen-containing ring metal chelate complex represented by the following formula (A) is preferable.
- R 2 to R 7 in the general formula (A) are each independently a hydrogen atom, a deuterium atom, a halogen atom, an oxy group, an amino group, a hydrocarbon group having 1 to 40 carbon atoms, an alkoxy group, an aryloxy group, It is an alkoxycarbonyl group or an aromatic heterocyclic group, and these may be substituted.
- the halogen atom include fluorine, chlorine, bromine, iodine and the like.
- the optionally substituted amino group include an alkylamino group, an arylamino group, and an aralkylamino group.
- the alkoxycarbonyl group is represented as —COOY ′, and examples of Y ′ include the same as the alkyl group.
- the alkylamino group and the aralkylamino group are represented as —NQ 1 Q 2 . Specific examples of Q 1 and Q 2 are independently the same as those described for the alkyl group and the aralkyl group, and preferred examples are also the same.
- One of Q 1 and Q 2 may be a hydrogen atom or a deuterium atom.
- the arylamino group is represented as —NAr 1 Ar 2, and specific examples of Ar 1 and Ar 2 are the same as those described for the non-condensed aromatic hydrocarbon group and the condensed aromatic hydrocarbon group, respectively. .
- One of Ar 1 and Ar 2 may be a hydrogen atom or a deuterium atom.
- M is aluminum (Al), gallium (Ga) or indium (In), and is preferably In.
- L in the above formula (A) is a group represented by the following formula (A ′) or (A ′′).
- R 8 to R 12 are each independently a hydrogen atom, a deuterium atom, or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are cyclic A structure may be formed.
- R 13 to R 27 are each independently a hydrogen atom, a deuterium atom or a substituted or unsubstituted hydrocarbon group having 1 to 40 carbon atoms, and groups adjacent to each other are An annular structure may be formed.
- Examples of the hydrocarbon group having 1 to 40 carbon atoms represented by R 8 to R 12 and R 13 to R 27 in the formula (A ′) and the formula (A ′′) include R 2 to R 7 in the formula (A).
- the divalent group includes a tetramethylene group, a pentamethylene group, a hexamethylene group, diphenylmethane-2,2 Examples include a '-diyl group, a diphenylethane-3,3'-diyl group, and a diphenylpropane-4,4'-diyl group.
- 8-hydroxyquinoline or a metal complex of its derivative, an oxadiazole derivative, or a nitrogen-containing heterocyclic derivative is preferable.
- a metal chelate oxinoid compound containing a chelate of oxine (generally 8-quinolinol or 8-hydroxyquinoline), for example, tris (8-quinolinol) aluminum is used.
- 8-quinolinol or 8-hydroxyquinoline a metal chelate oxinoid compound containing a chelate of oxine
- tris (8-quinolinol) aluminum is used.
- an oxadiazole derivative the following can be mentioned.
- Ar 17, Ar 18, Ar 19, Ar 21, Ar 22 and Ar 25 represents an or without an aromatic hydrocarbon group or fused aromatic hydrocarbon group having a substituent
- Ar 17 Ar 18 , Ar 19 and Ar 21 , Ar 22 and Ar 25 may be the same as or different from each other.
- the aromatic hydrocarbon group or the condensed aromatic hydrocarbon group include a phenyl group, a naphthyl group, a biphenyl group, an anthranyl group, a perylenyl group, and a pyrenyl group.
- substituent for these include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group.
- Ar 20 , Ar 23 and Ar 24 each represent a divalent aromatic hydrocarbon group or a condensed aromatic hydrocarbon group with or without a substituent, and Ar 23 and Ar 24 may be the same or different from each other. Also good.
- the divalent aromatic hydrocarbon group or condensed aromatic hydrocarbon group include a phenylene group, a naphthylene group, a biphenylene group, an anthranylene group, a peryleneylene group, and a pyrenylene group.
- substituent for these include an alkyl group having 1 to 10 carbon atoms, an alkoxy group having 1 to 10 carbon atoms, and a cyano group.
- electron transfer compounds those having good thin film forming properties are preferably used.
- Specific examples of these electron transfer compounds include the following.
- the nitrogen-containing heterocyclic derivative as the electron transfer compound is a nitrogen-containing heterocyclic derivative composed of an organic compound having the following general formula, and includes a nitrogen-containing compound that is not a metal complex. Examples thereof include a 5-membered ring or 6-membered ring containing a skeleton represented by the following formula (B) and a structure represented by the following formula (C).
- X represents a carbon atom or a nitrogen atom.
- Z 1 and Z 2 each independently represents an atomic group capable of forming a nitrogen-containing heterocycle.
- the nitrogen-containing heterocyclic derivative is more preferably an organic compound having a nitrogen-containing aromatic polycyclic group consisting of a 5-membered ring or a 6-membered ring. Further, in the case of such a nitrogen-containing aromatic polycyclic group having a plurality of nitrogen atoms, the nitrogen-containing compound having a skeleton in which the above formulas (B) and (C) or the above formula (B) and the following formula (D) are combined. Aromatic polycyclic organic compounds are preferred.
- the nitrogen-containing group of the nitrogen-containing aromatic polycyclic organic compound is selected from, for example, nitrogen-containing heterocyclic groups represented by the following general formula.
- R is an aromatic hydrocarbon group or condensed aromatic hydrocarbon group having 6 to 40 carbon atoms, an aromatic heterocyclic group or condensed aromatic heterocyclic group having 3 to 40 carbon atoms, 1 to 20 is an alkyl group or an alkoxy group having 1 to 20 carbon atoms, n is an integer of 0 to 5, and when n is an integer of 2 or more, a plurality of R may be the same or different from each other.
- preferred specific compounds include nitrogen-containing heterocyclic derivatives represented by the following formula.
- HAr-L 1 -Ar 1 -Ar 2 In the above formula, HAr is an optionally substituted nitrogen-containing heterocyclic group having 3 to 40 carbon atoms, and L 1 is a single bond or optionally having 6 to 40 carbon atoms.
- HAr is selected from the following group, for example.
- L 1 is selected from the following group, for example.
- Ar 1 is selected from, for example, the following arylanthranyl groups.
- R 1 to R 14 each independently represents a hydrogen atom, a deuterium atom, a halogen atom, an alkyl group having 1 to 20 carbon atoms, an alkoxy group having 1 to 20 carbon atoms, or an alkyl group having 6 to 40 carbon atoms.
- Ar 3 is an optionally substituted aromatic hydrocarbon group having 6 to 40 carbon atoms, a condensed aromatic hydrocarbon group, an aromatic heterocyclic group having 3 to 40 carbon atoms or a condensed aromatic group.
- R 1 to R 8 may be nitrogen-containing heterocyclic derivatives each of which is a hydrogen atom or a deuterium atom.
- Ar 2 is selected from the following group, for example.
- the nitrogen-containing aromatic polycyclic organic compound as the electron transfer compound, the following compounds (see JP-A-9-3448) are also preferably used.
- R 1 to R 4 each independently represent a hydrogen atom, a deuterium atom, a substituted or unsubstituted aliphatic group, a substituted or unsubstituted aliphatic cyclic group, or a substituted or unsubstituted carbocycle.
- X 1 and X 2 each independently represents an oxygen atom, a sulfur atom, or a dicyanomethylene group.
- R 1 , R 2 , R 3 and R 4 are the same or different groups, and are an aromatic hydrocarbon group or a condensed aromatic hydrocarbon group represented by the following formula.
- R 5 , R 6 , R 7 , R 8 and R 9 are the same or different from each other, and hydrogen atom, deuterium atom, or at least one of them is a saturated or unsaturated alkoxyl group, alkyl A group, an amino group, or an alkylamino group.
- the electron transfer compound may be a polymer compound containing the nitrogen-containing heterocyclic group or the nitrogen-containing heterocyclic derivative.
- the electron transport layer preferably contains at least one of nitrogen-containing heterocyclic derivatives represented by the following formulas (201) to (203).
- R represents a hydrogen atom, a deuterium atom, an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group, a substituted group.
- a pyridyl group which may have a group, a quinolyl group which may have a substituent, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a substituent.
- R 1 has an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group, an optionally substituted pyridyl group, and a substituent.
- An optionally substituted quinolyl group, an optionally substituted alkyl group having 1 to 20 carbon atoms, or an alkoxy group having 1 to 20 carbon atoms, R 2 and R 3 each independently have a hydrogen atom, a deuterium atom, an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms, a condensed aromatic hydrocarbon group, or a substituent.
- Ar 1 has an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group, an optionally substituted pyridinylene group, or a substituent.
- Ar 2 is an optionally substituted aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group, or an optionally substituted pyridyl group.
- Ar 3 has an aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group which may have a substituent, a pyridyl group which may have a substituent, or a substituent.
- An optionally substituted quinolyl group, an optionally substituted alkyl group having 1 to 20 carbon atoms, an optionally substituted alkoxy group having 1 to 20 carbon atoms, or —Ar 1 —Ar 2 Groups represented by Ar 1 and Ar 2 are the same as defined above.
- R represents a hydrogen atom, a deuterium atom, an aromatic hydrocarbon group having 6 to 60 carbon atoms or a condensed aromatic hydrocarbon group which may have a substituent.
- a pyridyl group which may have a substituent a quinolyl group which may have a substituent, an alkyl group having 1 to 20 carbon atoms which may have a substituent, or a substituent. It may be an alkoxy group having 1 to 20 carbon atoms.
- the film thickness of the electron injection layer or the electron transport layer is not particularly limited, but is preferably 1 nm to 100 nm.
- an insulator or a semiconductor as an inorganic compound as a constituent of the electron injection layer. If the electron injection layer is made of an insulator or a semiconductor, current leakage can be effectively prevented and the electron injection property can be improved.
- an insulator it is preferable to use at least one metal compound selected from the group consisting of alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides and alkaline earth metal halides. If the electron injection layer is composed of these alkali metal chalcogenides or the like, it is preferable in that the electron injection property can be further improved.
- preferable alkali metal chalcogenides include, for example, Li 2 O, K 2 O, Na 2 S, Na 2 Se, and Na 2 O
- preferable alkaline earth metal chalcogenides include, for example, CaO, BaO. , SrO, BeO, BaS and CaSe.
- preferable alkali metal halides include, for example, LiF, NaF, KF, LiCl, KCl, and NaCl.
- preferable alkaline earth metal halides include fluorides such as CaF 2 , BaF 2 , SrF 2 , MgF 2 and BeF 2 , and halides other than fluorides.
- the inorganic compound constituting the electron injection layer is preferably a microcrystalline or amorphous insulating thin film. If the electron injection layer is composed of these insulating thin films, a more uniform thin film is formed, and pixel defects such as dark spots can be reduced.
- examples of such inorganic compounds include alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides.
- the preferred thickness of the layer is about 0.1 nm to 15 nm.
- the electron injection layer in this invention contains the above-mentioned reducing dopant, it is preferable.
- an aromatic amine compound for example, an aromatic amine derivative represented by the following general formula (I) is preferably used.
- Ar 1 to Ar 4 represent a substituted or unsubstituted aromatic hydrocarbon group having 6 to 50 ring carbon atoms or a condensed aromatic hydrocarbon group, a substituted or unsubstituted nuclear atom number of 5 to 50 aromatic heterocyclic groups or condensed aromatic heterocyclic groups, or a group in which these aromatic hydrocarbon groups or condensed aromatic hydrocarbon groups are combined with aromatic heterocyclic groups or condensed aromatic heterocyclic groups .
- aromatic amines of the following general formula (II) are also preferably used for forming the hole injection layer or the hole transport layer.
- the light emitting layer contains a charge injection auxiliary material.
- a light emitting layer is formed using a host material having a wide energy gap, the difference between the ionization potential (Ip) of the host material and Ip of the hole injection / transport layer, etc. increases, and holes are injected into the light emitting layer. This may make it difficult to increase the driving voltage for obtaining sufficient luminance.
- by adding a hole injection / transport charge injection auxiliary agent to the light emitting layer hole injection into the light emitting layer can be facilitated and the driving voltage can be lowered.
- a general hole injection / transport material or the like can be used as the charge injection auxiliary agent.
- Specific examples include triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives and pyrazolone derivatives, phenylenediamine derivatives, arylamine derivatives, amino-substituted chalcone derivatives, oxazole derivatives, fluorenone derivatives, hydrazone derivatives, stilbenes.
- Derivatives, silazane derivatives, polysilane-based, aniline-based copolymers, conductive polymer oligomers (particularly thiophene oligomers), and the like can be given.
- hole-injecting material examples include the above materials, but porphyrin compounds, aromatic tertiary amine compounds and styrylamine compounds, particularly aromatic tertiary amine compounds are preferred.
- NPD 4,4′-bis (N- (1-naphthyl) -N-phenylamino) biphenyl
- MTDATA triphenylamine 4,4 ′, 4 ′′ -tris (N- (3-methylphenyl) -N-phenylamino) triphenylamine
- a hexaazatriphenylene derivative or the like can also be suitably used as the hole injecting material.
- each layer of the organic EL element of the present invention is not particularly limited. Conventionally known methods such as vacuum deposition and spin coating can be used.
- the organic thin film layer containing the compounds represented by the above formulas (1) to (4) and (1 ′) used for the organic EL device of the present invention is prepared by vacuum deposition, molecular beam deposition (MBE) or The solution can be formed by a known method such as a dipping method, a spin coating method, a casting method, a bar coating method, or a roll coating method.
- each organic layer of the organic EL device of the present invention is not particularly limited. Generally, if the film thickness is too thin, defects such as pinholes are likely to occur. Conversely, if it is too thick, a high applied voltage is required and the efficiency is deteriorated. Therefore, the range of several nm to 1 ⁇ m is usually preferable.
- intermediate 1-13 (7.9 g, yield 62%).
- Intermediate 1-13 (7 g, 17 mmol), 2-bromocarbazole (4.2 g, 17 mmol), tetrakistriphenylphosphine palladium (0.4 g, 0.3 mmol), toluene (25 mL), dimethoxyethane (25 mL) 2M aqueous sodium carbonate solution (25 mL) was added in this order, and the mixture was heated with stirring at 80 ° C. for 8 hours. The organic layer of the reaction solution was separated, and the solvent was distilled off with an evaporator.
- Example 1-1 (Production of Organic EL Device) A glass substrate with an ITO transparent electrode of 25 mm ⁇ 75 mm ⁇ thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The glass substrate with the transparent electrode line after washing is attached to the substrate holder of the vacuum deposition apparatus, and the electron-accepting compound (C-) is first covered so that the transparent electrode is covered on the surface where the transparent electrode line is formed. 1) was vapor-deposited to form a C-1 film having a thickness of 5 nm.
- the following aromatic amine derivative (X1) was vapor-deposited as a first hole transport material to form a first hole transport layer having a thickness of 50 nm.
- the following aromatic amine derivative (X2) was deposited as a second hole transport material to form a second hole transport layer having a thickness of 60 nm.
- Compound 1 obtained in Synthesis Example 1-1 was deposited on the second hole transport layer to form a light emitting layer having a thickness of 45 nm.
- the following compound (D3) was co-deposited as a phosphorescent material.
- the concentration of Compound D3 was 8.0% by mass.
- This co-deposited film functions as a light emitting layer.
- the following compound (ET2) was formed to a thickness of 30 nm. This ET1 film functions as an electron transport layer.
- LiF was used as an electron injecting electrode (cathode), and the film thickness was set to 1 nm at a film forming rate of 0.1 angstrom / min.
- Metal Al was vapor-deposited on this LiF film, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.
- Table 1 shows the results of measuring the light emission efficiency of the obtained organic EL device at an initial luminance of 2000 cd / m 2 , room temperature, and DC constant current driving. Further, Table 1 shows the results of measuring the half life of light emission at an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving.
- Example 1-1 an organic EL device was produced in the same manner as in Example 1-1 except that the light emitting layer was formed using the compounds shown in Table 1 instead of using Compound 1-1.
- the measurement results of luminous efficiency and half-life are shown in Table 1.
- Comparative Example 1-4 An organic EL device was produced in the same manner as in Example 1-1 except that in Example 1-1, the light emitting layer was formed using Compound 1-D instead of Compound 1-1. In the organic EL device obtained in Comparative Example 1-4, no light emission from the phosphorescent material (Compound D3) was observed.
- Compounds 1-A and 1-B are compounds specifically described in Patent Document 9, and Compounds 1-C and 1-D are compounds specifically described in Patent Document 7.
- the compounds 1-A and 1-C are used, the inside of the light emitting layer becomes excessive in holes and is not balanced with electrons.
- the electron transportability is inferior to that of the biscarbazole derivative of the present invention, so that excess holes cannot be eliminated. From the above results, it is clear that the compound of the present invention is superior in terms of luminous efficiency and lifetime as compared with the compound used in the comparative example.
- an appropriate condensed ring to the biscarbazole derivative skeleton in order to improve the performance of the host material, and an aromatic condensed ring such as fluoranthene or benzophenanthrene may be selected as the condensed ring. all right.
- Example 2-1 (Production of organic EL device) A glass substrate with an ITO transparent electrode of 25 mm ⁇ 75 mm ⁇ thickness 1.1 mm (manufactured by Geomatic Co., Ltd.) was subjected to ultrasonic cleaning in isopropyl alcohol for 5 minutes and then UV ozone cleaning for 30 minutes. The glass substrate with the transparent electrode line after washing is attached to the substrate holder of the vacuum deposition apparatus, and the electron-accepting compound (C-) is first covered so that the transparent electrode is covered on the surface where the transparent electrode line is formed. 1) was vapor-deposited to form a C-1 film having a thickness of 5 nm.
- the following aromatic amine derivative (X1) was vapor-deposited as a first hole transport material to form a first hole transport layer having a thickness of 50 nm.
- the following aromatic amine derivative (X2) was deposited as a second hole transport material to form a second hole transport layer having a thickness of 60 nm.
- the compound 2-1 obtained in Synthesis Example 2-1 was vapor-deposited on the second hole transport layer to form a light emitting layer having a thickness of 45 nm.
- the following compound (D3) was co-deposited as a phosphorescent material.
- the concentration of Compound D3 was 8.0% by mass.
- This co-deposited film functions as a light emitting layer.
- the following compound (ET2) was formed to a thickness of 30 nm. This ET1 film functions as an electron transport layer.
- LiF was used as an electron injecting electrode (cathode), and the film thickness was set to 1 nm at a film forming rate of 0.1 angstrom / min.
- Metal Al was vapor-deposited on this LiF film, and a metal cathode was formed with a film thickness of 80 nm to produce an organic EL device.
- Table 2 shows the results of measuring the luminous efficiency of the obtained organic EL device with an initial luminance of 2000 cd / m 2 , room temperature, and DC constant current driving. Further, Table 1 shows the results of measuring the half life of light emission at an initial luminance of 5000 cd / m 2 , room temperature, and DC constant current driving.
- Example 2-1 an organic EL device was produced in the same manner as in Example 2-1, except that the light emitting layer was formed using the compounds shown in Table 2 instead of using the compound 2-1.
- the organic EL device of the present invention using the compounds 2-1 to 2-5 showed good luminous efficiency and lifetime characteristics.
- Patent Document 9 the compounds 2-A and 2-B described in the prior art (Patent Document 9) were used, the device lifetime was shortened. This seems to be due to the presence of an amino substituent that is inferior in electron resistance, or the fact that the active site of the fluorenyl group is not protected.
- Compound C causes higher voltage and lower efficiency than the device of the present invention.
- an amino group, a fluorenyl group, and a naphthyl group cannot obtain sufficient characteristics as a group bonded to the 9-position of carbazole, and it is important to select an aryl substituent or a condensed ring.
- the present invention can be used as an organic EL element having a long life, high luminous efficiency, and capable of being driven at a low voltage required for power saving, and an organic EL element material for realizing the organic EL element.
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Abstract
Description
従来、有機EL素子においては、蛍光型、及び燐光型の発光メカニズムに応じ、最適な素子設計がなされてきた。特に燐光型の有機EL素子については、その発光特性から、蛍光素子技術の単純な転用では高性能な素子が得られないことが知られている。その理由は、一般的に以下のように考えられている。
まず、燐光発光は、三重項励起子を利用した発光であるため、発光層に用いる化合物のエネルギーギャップが大きくなくてはならない。何故なら、ある化合物のエネルギーギャップ(以下、一重項エネルギーともいう。)の値は、通常、その化合物の三重項エネルギー(本発明では、最低励起三重項状態と基底状態とのエネルギー差をいう。)の値よりも大きいからである。
また、蛍光素子で有用であった酸化耐性や還元耐性の高い炭化水素系の化合物はπ電子雲の広がりが大きいため、エネルギーギャップが小さい。そのため、燐光型の有機EL素子では、このような炭化水素系の化合物が選択され難く、酸素や窒素などのヘテロ原子を含んだ有機化合物が選択され、その結果、燐光型の有機EL素子は、蛍光型の有機EL素子と比較して寿命が短いという問題を有する。
さらに、燐光発光性ドーパント材料の三重項励起子の励起子緩和速度が一重項励起子と比較して非常に長いことも素子性能に大きな影響を与える。即ち、一重項励起子からの発光は、発光に繋がる緩和速度が速いため、発光層の周辺層(例えば、正孔輸送層や電子輸送層)への励起子の拡散が起きにくく、効率的な発光が期待される。一方、三重項励起子からの発光は、スピン禁制であり緩和速度が遅いため、周辺層への励起子の拡散が起きやすく、特定の燐光発光性化合物以外からは熱的なエネルギー失活が起きてしまう。つまり、電子、及び正孔の再結合領域のコントロールが蛍光型の有機EL素子よりも重要である。
以上のような理由から燐光型の有機EL素子の高性能化には、蛍光型の有機EL素子と異なる材料選択、及び素子設計が必要になっている。
[1] 下記式(1)で表されるビスカルバゾール誘導体。
Y1~Y16は互いに独立してC(R)または窒素原子を表し、Rはそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。
L1及びL2は互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。
但し、A1、A2及びRのうち少なくとも1つは置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のジベンゾトリフェニレニル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のベンゾクリセニル基、置換もしくは無置換のピセニル基、置換もしくは無置換のベンゾ[b]フルオランテニル基、置換もしくは無置換のフェナントレニル基、置換もしくは無置換のビナフチル基、置換もしくは無置換のジベンゾフェナントレニル基、置換もしくは無置換のナフトトリフェニレニル基、置換もしくは無置換のベンゾフルオレニル基又はナフチル基を表す。
また、Y1~Y16が全てC(R)であり、Rが水素であり、Y6とY11が単結合で結合し、L1及びL2が単結合であり、A1がフェナントレニル基の場合、A2はフェニル基、ビフェニリル基又はナフチル基である。さらに、Y1~Y16が全てC(R)であり、Rが水素であり、Y6とY11が単結合で結合し、L1及びL2が単結合であり、A1がナフチル基の場合、A1とA2は互いに異なる。)
[2] 上記式(1)において、A1及びA2の少なくとも一方が、置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のジベンゾトリフェニレニル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のベンゾクリセニル基、置換もしくは無置換のピセニル基、又は置換もしくは無置換のベンゾ[b]フルオランテニル基、置換もしくは無置換のフェナントレニル基、置換もしくは無置換のビナフチル基、置換もしくは無置換のジベンゾフェナントレニル基、置換もしくは無置換のナフトトリフェニレニル基、又は置換もしくは無置換のベンゾフルオレニル基である[1]に記載のビスカルバゾール誘導体。
[3] 下記式(2)で表される[1]又は[2]に記載のビスカルバゾール誘導体。
[4] 下記式(3)又は(4)で表される[1]又は[2]に記載のビスカルバゾール誘導体。
[5] 前記-L1-A1と-L2-A2とが互いに異なる[1]~[4]のいずれかに記載のビスカルバゾール誘導体。
[6] 前記L1及びL2が2価の連結基である[1]~[5]のいずれかに記載のビスカルバゾール誘導体。
[7] 前記A1が、置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のジベンゾトリフェニレニル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のベンゾクリセニル基、置換もしくは無置換のピセニル基、又は置換もしくは無置換のベンゾ[b]フルオランテニル基、置換もしくは無置換のフェナントレニル基、置換もしくは無置換のビナフチル基、置換もしくは無置換のジベンゾフェナントレニル基、置換もしくは無置換のナフトトリフェニレニル基、又は置換もしくは無置換のベンゾフルオレニル基、であり、かつ、A2が、環形成炭素数6~30の置換もしくは無置換の芳香族炭化水素基である[1]~[6]のいずれかに記載のビスカルバゾール誘導体。
[8] 下記式(1a)で表されるビスカルバゾール誘導体。
Y1a~Y16aは互いに独立してC(R)または窒素原子を表し、Rはそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。L1a及びL2aは互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。)
[9] [1]~[8]のいずれかに記載のビスカルバゾール誘導体からなる有機エレクトロルミネッセンス素子用材料。
[10] 陰極と陽極の間に発光層を含む複数の有機薄膜層を有し、前記有機薄膜層のうち少なくとも1層が[1]~[9]のいずれかに記載のビスカルバゾール誘導体を含む有機エレクトロルミネッセンス素子。
[11] 陰極と陽極の間に発光層を含む複数の有機薄膜層を有し、前記有機薄膜層のうち少なくとも1層が、下記式(10)で表されるビスカルバゾール誘導体を含む有機エレクトロルミネッセンス素子。
Y1'~Y16'は互いに独立してC(R’)または窒素原子を表し、R’はそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。
L1'及びL2'は互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。)
[12] 前記発光層において前記ビスカルバゾール誘導体をホスト材料として含む[10]又は[11]に記載の有機エレクトロルミネッセンス素子。
[13] 前記発光層が燐光材料を含有する[12]に記載の有機エレクトロルミネッセンス素子。
[14] 前記発光層がホスト材料と燐光材料を有し、燐光材料がイリジウム(Ir),オスミウム(Os)、白金(Pt)から選択される金属原子のオルトメタル化錯体である[13]に記載の有機エレクトロルミネッセンス素子。
[15] 陰極と発光層の間に電子注入層を有し、該電子注入層が含窒素環誘導体を含む[14]に記載の有機エレクトロルミネッセンス素子。
[16] 陰極と発光層の間に電子輸送層を有し、該電子輸送層が前記ビスカルバゾール誘導体を含む[15]に記載の有機エレクトロルミネッセンス素子。
[17] 陽極と発光層の間に正孔輸送層を有し、該正孔輸送層が前記ビスカルバゾール誘導体を含む[16]に記載の有機エレクトロルミネッセンス素子。
[18] 陰極と有機薄膜層との界面に還元性ドーパントを含有する[17]に記載の有機エレクトロルミネッセンス素子。
[19] [10]~[18]のいずれかに記載の有機エレクトロルミネッセンス素子を備えることを特徴とする照明装置。
[20] [10]~[19]のいずれかに記載の有機エレクトロルミネッセンス素子を備えることを特徴とする表示装置。
(有機EL素子の構成)
まず、有機EL素子の素子構成について説明する。
有機EL素子の代表的な素子構成としては、
(1)陽極/発光層/陰極
(2)陽極/正孔注入層/発光層/陰極
(3)陽極/発光層/電子注入・輸送層/陰極
(4)陽極/正孔注入層/発光層/電子注入・輸送層/陰極
(5)陽極/有機半導体層/発光層/陰極
(6)陽極/有機半導体層/電子障壁層/発光層/陰極
(7)陽極/有機半導体層/発光層/付着改善層/陰極
(8)陽極/正孔注入・輸送層/発光層/電子注入・輸送層/陰極
(9)陽極/絶縁層/発光層/絶縁層/陰極
(10)陽極/無機半導体層/絶縁層/発光層/絶縁層/陰極
(11)陽極/有機半導体層/絶縁層/発光層/絶縁層/陰極
(12)陽極/絶縁層/正孔注入・輸送層/発光層/絶縁層/陰極
(13)陽極/絶縁層/正孔注入・輸送層/発光層/電子注入・輸送層/陰極
などの構造を挙げることができる。
上記の中で(8)の構成が好ましく用いられるが、もちろんこれらに限定されるものではない。
また、各発光層の間に、燐光発光層で生成された励起子が蛍光発光層に拡散することを防ぐ目的で、スペース層を有していてもよい。
有機EL素子1は、透明な基板2と、陽極3と、陰極4と、陽極3と陰極4との間に配置された有機薄膜層10と、を有する。
有機薄膜層10は、ホスト材料としての燐光ホスト及び燐光材料としての燐光ドーパントを含む燐光発光層5を有するが、燐光発光層5と陽極3との間に正孔注入・輸送層6等、燐光発光層5と陰極4との間に電子注入・輸送層7等を備えていてもよい。
また、燐光発光層5の陽極3側に電子障壁層を、燐光発光層5の陰極4側に正孔障壁層を、それぞれ設けてもよい。
これにより、電子や正孔を燐光発光層5に閉じ込めて、燐光発光層5における励起子の生成確率を高めることができる。
(a)正孔輸送層/発光層(/電子輸送層)
(b)正孔輸送層/第一燐光発光層/第二燐光発光層(/電子輸送層)
(c)正孔輸送層/燐光発光層/スペース層/蛍光発光層(/電子輸送層)
(d)正孔輸送層/第一燐光発光層/第二燐光発光層/スペース層/蛍光発光層(/電子輸送層)
(e)正孔輸送層/第一燐光発光層/スペース層/第二燐光発光層/スペース層/蛍光発光層(/電子輸送層)
(f)正孔輸送層/燐光発光層/スペース層/第一蛍光発光層/第二蛍光発光層(/電子輸送層)
陽極/第一発光ユニット/中間層/第二発光ユニット/陰極
ここで、上記第一発光ユニット及び第二発光ユニットとしては、例えば、それぞれ独立に上述の発光ユニットと同様のものを選択することができる。
上記中間層は、一般的に、中間電極、中間導電層、電荷発生層、電子引抜層、接続層、中間絶縁層とも呼ばれ、第一発光ユニットに電子を、第二発光ユニットに正孔を供給する、公知の材料構成を用いることができる。
言い換えると、本明細書において、蛍光ホストとは、蛍光ドーパントを含有する蛍光発光層を構成する材料を意味し、蛍光発光材料のホストにしか利用できないものを意味しているわけではない。
同様に燐光ホストとは、燐光ドーパントを含有する燐光発光層を構成する材料を意味し、燐光材料のホストにしか利用できないものを意味しているわけではない。
本発明の有機EL素子は、透光性の基板上に作製する。ここでいう透光性基板は有機EL素子を支持する基板であり、400nm~700nmの可視領域の光の透過率が50%以上で平滑な基板が好ましい。
具体的には、ガラス板、ポリマー板等が挙げられる。
ガラス板としては、特にソーダ石灰ガラス、バリウム・ストロンチウム含有ガラス、鉛ガラス、アルミノケイ酸ガラス、ホウケイ酸ガラス、バリウムホウケイ酸ガラス、石英等を原料として用いてなるものを挙げられる。
またポリマー板としては、ポリカーボネート、アクリル、ポリエチレンテレフタレート、ポリエーテルサルファイド、ポリサルフォン等を原料として用いてなるものを挙げることができる。
有機EL素子の陽極は、正孔を正孔注入層、正孔輸送層又は発光層に注入する役割を担うものであり、4.5eV以上の仕事関数を有することが効果的である。
陽極材料の具体例としては、酸化インジウム錫合金(ITO)、酸化錫(NESA)、酸化インジウム亜鉛酸化物、金、銀、白金、銅等が挙げられる。
陽極はこれらの電極物質を蒸着法やスパッタリング法等の方法で薄膜を形成させることにより作製することができる。
本実施形態のように、発光層からの発光を陽極から取り出す場合、陽極の可視領域の光の透過率を10%より大きくすることが好ましい。また、陽極のシート抵抗は、数百Ω/□以下が好ましい。陽極の膜厚は、材料にもよるが、通常10nm~1μm、好ましくは10nm~200nmの範囲で選択される。
陰極材料は特に限定されないが、具体的にはインジウム、アルミニウム、マグネシウム、マグネシウム-インジウム合金、マグネシウム-アルミニウム合金、アルミニウム-リチウム合金、アルミニウム-スカンジウム-リチウム合金、マグネシウム-銀合金等が使用できる。
陰極も、陽極と同様に、蒸着法やスパッタリング法等の方法で薄膜を形成させることにより作製することができる。また、陰極側から、発光を取り出す態様を採用することもできる。
有機EL素子の発光層は以下の機能を併せ持つものである。
すなわち、
(1)注入機能;電界印加時に陽極又は正孔注入層より正孔を注入することができ、陰極又は電子注入層より電子を注入することができる機能、
(2)輸送機能;注入した電荷(電子と正孔)を電界の力で移動させる機能、
(3)発光機能;電子と正孔の再結合の場を提供し、これを発光につなげる機能、
がある。
この発光層を形成する方法としては、例えば蒸着法、スピンコート法、LB法等の公知の方法を適用することができる。
ここで分子堆積膜とは、気相状態の材料化合物から沈着され形成された薄膜や、溶液状態又は液相状態の材料化合物から固体化され形成された膜のことであり、通常この分子堆積膜は、LB法により形成された薄膜(分子累積膜)とは凝集構造、高次構造の相違や、それに起因する機能的な相違により区分することができる。
また、樹脂等の結着剤と材料化合物とを溶剤に溶かして溶液とした後、これをスピンコート法等により薄膜化することによっても、発光層を形成することができる。
本発明の有機EL素子は、陰極と陽極の間に発光層を含む複数の有機薄膜層を有し、この有機薄膜層のうち少なくとも1層がビスカルバゾール誘導体を含む。なお、本明細書中、「水素」は重水素も含むものである。また、本発明のビスカルバゾール誘導体は、分子中に二つのみのカルバゾール構造を有するものが好ましい。
本発明のビスカルバゾール誘導体は、特定の位置に置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のジベンゾトリフェニレニル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のベンゾクリセニル基、置換もしくは無置換のピセニル基、又は置換もしくは無置換のベンゾ[b]フルオランテニル基、置換もしくは無置換のベンゾフラニル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のベンゾチオフェニル基、置換もしくは無置換のジベンゾチオフェニル基、置換もしくは無置換のフェナントレニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のビナフチル基、置換もしくは無置換のベンゾナフトフラニル基、置換もしくは無置換のベンゾナフトチオフェニル基、置換もしくは無置換のジベンゾフェナントレニル基、置換もしくは無置換のナフトトリフェニレニル基、置換もしくは無置換のベンゾフルオランテニル基、置換もしくは無置換のベンゾフルオレニル基又は置換もしくは無置換のフェニル基を有し、具体的には下記式(1)~(4)、(1’)、(1a)及び(10)のいずれかで表される。
Y1~Y16は互いに独立してC(R)または窒素原子を表し、Rはそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。
L1及びL2は互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。
但し、A1、A2及びRのうち少なくとも1つは置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のジベンゾトリフェニレニル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のベンゾクリセニル基、置換もしくは無置換のピセニル基、置換もしくは無置換のベンゾ[b]フルオランテニル基、置換もしくは無置換のフェナントレニル基、置換もしくは無置換のビナフチル基、置換もしくは無置換のジベンゾフェナントレニル基、置換もしくは無置換のナフトトリフェニレニル基、置換もしくは無置換のベンゾフルオレニル基又はナフチル基を表す。
また、Y1~Y16が全てC(R)であり、Rが水素であり、Y6とY11が単結合で結合し、L1及びL2が単結合であり、A1がフェナントレニル基の場合、A2はフェニル基、ビフェニリル基又はナフチル基である。さらに、Y1~Y16が全てC(R)であり、Rが水素であり、Y6とY11が単結合で結合し、L1及びL2が単結合であり、A1がナフチル基の場合、A1とA2は互いに異なる。)
また、Y5~Y8のうち1つはC(R)であり、Y9~Y12のうち1つはC(R)であり、これらのRは互いに結合する結合手を表す。
式(1)及び(1’)における複数のRは、互いに同じでも異なっていてもよい。
また、Y5a~Y8aのうち1つはC(R)であり、Y9a~Y12aのうち1つはC(R)であり、これらのRは互いに結合する結合手を表す。
式(1a)における複数のRは、互いに同じでも異なっていてもよい。
また、Y5'~Y8'のうち1つはC(R’)であり、Y9'~Y12'のうち1つはC(R’)であり、これらのR’は互いに結合する結合手を表す。
式(10)における複数のR’は、互いに同じでも異なっていてもよい。
Y1~Y16は互いに独立してC(R)または窒素原子を表し、Rはそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。
L1及びL2は互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。
但し、A1、A2及びRのうち少なくとも1つは置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のジベンゾトリフェニレニル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のベンゾクリセニル基、置換もしくは無置換のピセニル基、又は置換もしくは無置換のベンゾ[b]フルオランテニル基、置換もしくは無置換のベンゾフラニル基、置換もしくは無置換のジベンゾフラニル基、置換もしくは無置換のベンゾチオフェニル基、置換もしくは無置換のジベンゾチオフェニル基、置換もしくは無置換のフェナントレニル基、置換もしくは無置換のフルオレニル基、置換もしくは無置換のビナフチル基、置換もしくは無置換のベンゾナフトフラニル基、置換もしくは無置換のベンゾナフトチオフェニル基、置換もしくは無置換のジベンゾフェナントレニル基、置換もしくは無置換のナフトトリフェニレニル基、又は置換もしくは無置換のベンゾフルオレニル基、置換もしくは無置換のフェニル基を表す。また、Y1~Y16が全てC(R)であり、Rが水素であり、Y6とY11が単結合で結合し、L1及びL2が単結合であり、A1がフェナントレニル基の場合、A2はフェナントレニル基ではない。
さらに、Y1~Y16が全てC(R)であり、Y6とY11が単結合で結合し、L1とL2が単結合である場合、Rはいずれもフルオレニル基ではなく、さらにA1がフルオレニル基の場合、A2はフェニル基、ナフチル基、又はフルオレニル基ではない。)
Y1a~Y16aは互いに独立してC(R)または窒素原子を表し、Rはそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。L1a及びL2aは互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。)
式(1a)及び式(a)におけるA1a、A2a、Y1a~Y16a、L1a、L2a及びRaの詳細は、それぞれ一般式(1)におけるA1、A2、Y1~Y16、L1、L2及びRと同様である。
ただし、式(1a)においてA1a及びA2aのどちらか一方が式(a)で表される基である場合、他方がトリフェニレニル基やクリセニル基のような分子量が大きい縮合環を有する基であると、化合物自体の分子量が大きくなるために蒸着温度が高くなり、熱分解成分が増加する傾向がある。従って、式(1a)においてA1a及びA2aのどちらか一方が式(a)で表される基である場合、他方は置換もしくは無置換のフルオランテニル基、又は置換もしくは無置換のフェナントレニル基であることが好ましい。
Y1'~Y16'は互いに独立してC(R’)または窒素原子を表し、R’はそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。
L1'及びL2'は互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。)
式(10)におけるA1'、A2'、L1'、L2'、Y1'~Y16'及びR’の詳細は、前記式(1)におけるA1、A2、L1、L2、Y1~Y16及びRとそれぞれ同様である。
また、前記式(1)~(4)及び(1’)において、A1及びA2は、それぞれ独立に、置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のジベンゾフラニル基、又は置換もしくは無置換のジベンゾチオフェニル基であることが好ましい。
さらに、前記式(1)~(4)及び(1’)における-L1-A1と-L2-A2とは互いに異なることが好ましい。
尚、A1、A2及びRのいずれかが表す置換もしくは無置換のフェニル基としては、炭素数10~30の芳香族炭化水素基により置換されたフェニル基が好ましく、ナフチルフェニル基が特に好ましい。
式(a)において、Y21及び/又はY25が窒素原子を表すことが好ましく、さらにY22及びY24がC(Ra)を表すことがより好ましい。
なお、隣接する環形成炭素上のRは互いに結合して環形成炭素と共に環構造を形成しても良い。
前記炭素数1~20の直鎖状、分岐鎖状又は環状のアルキレン基としては、例えば、エチレン基、プロピレン基、ブチレン基等が挙げられる。
前記炭素数1~20の直鎖状、分岐鎖状又は環状の2価の不飽和炭化水素基としては、例えば、1,3-ブタジエン-1,4-ジイル基等が挙げられる。
環形成炭素数6~30の2価の芳香族炭化水素基の具体例としては、上述の環形成炭素数6~30の芳香族炭化水素基として挙げられたものを2価基としたものが挙げられる。
また、環形成炭素数2~30の2価の芳香族複素環基の具体例としては、上述の環形成炭素数2~30の芳香族複素環基として挙げられたものを2価基としたものが挙げられる。
前記一般式(1)~(4)及び(1’)において、Y1~Y16が全てC(R)であると好ましい。
前記一般式(1)~(4)及び(1’)において、Y1~Y8、Y9~Y16のそれぞれにおいて、Rで表される置換基の数が0~2個であると好ましく、0又は1個であるとより好ましい。
また、本発明の有機EL素子は、正孔輸送層(正孔注入層)を有し、該正孔輸送層(正孔注入層)が本発明のビスカルバゾール誘導体を含有しても好ましい。
本発明において、前記燐光材料は、金属錯体を含有し、前記金属錯体は、Ir,Pt,Os,Au,Cu,Re及びRuから選択される金属原子と、配位子と、を有することが好ましい。特に、前記配位子は、オルトメタル結合を有することが好ましい。
燐光量子収率が高く、発光素子の外部量子効率をより向上させることができるという点で、Ir,Os及びPtから選ばれる金属原子を含有する化合物であると好ましく、イリジウム錯体、オスミウム錯体、白金錯体等の金属錯体であるとさらに好ましく、中でもイリジウム錯体及び白金錯体がより好ましく、オルトメタル化イリジウム錯体が最も好ましい。
好ましい金属錯体の具体例を、以下に示す。
このような発光波長の燐光材料(燐光ドーパント)を、本発明で用いる特定のホスト材料にドープして発光層を構成することにより、高効率な有機EL素子とできる。
本発明の有機EL素子は、陰極と有機薄膜層との界面領域に還元性ドーパントを有することも好ましい。
このような構成によれば、有機EL素子における発光輝度の向上や長寿命化が図られる。
還元性ドーパントとしては、アルカリ金属、アルカリ金属錯体、アルカリ金属化合物、アルカリ土類金属、アルカリ土類金属錯体、アルカリ土類金属化合物、希土類金属、希土類金属錯体、及び希土類金属化合物等から選ばれた少なくとも一種類が挙げられる。
アルカリ土類金属としては、Ca(仕事関数:2.9eV)、Sr(仕事関数:2.0eV~2.5eV)、Ba(仕事関数:2.52eV)等が挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
希土類金属としては、Sc、Y、Ce、Tb、Yb等が挙げられ、仕事関数が2.9eV以下のものが特に好ましい。
以上の金属のうち好ましい金属は、特に還元能力が高く、電子注入域への比較的少量の添加により、有機EL素子における発光輝度の向上や長寿命化が可能である。
アルカリ土類金属化合物としては、BaO、SrO、CaO及びこれらを混合したBaxSr1-xO(0<x<1)、BaxCa1-xO(0<x<1)等が挙げられ、BaO、SrO、CaOが好ましい。
希土類金属化合物としては、YbF3、ScF3、ScO3、Y2O3、Ce2O3、GdF3、TbF3等が挙げられ、YbF3、ScF3、TbF3が好ましい。
還元性ドーパントを層状に形成する場合は、界面の有機層である発光材料や電子注入材料を層状に形成した後に、還元ドーパントを単独で抵抗加熱蒸着法により蒸着し、好ましくは層の厚み0.1nm~15nmで形成する。
還元性ドーパントを島状に形成する場合は、界面の有機層である発光材料や電子注入材料を島状に形成した後に、還元ドーパントを単独で抵抗加熱蒸着法により蒸着し、好ましくは島の厚み0.05nm~1nmで形成する。
また、本発明の有機EL素子における、主成分と還元性ドーパントの割合としては、モル比で主成分:還元性ドーパント=5:1~1:5であると好ましく、2:1~1:2であるとさらに好ましい。
電子注入層又は電子輸送層は、発光層への電子の注入を助ける層であって、電子移動度が大きい。電子注入層はエネルギーレベルの急な変化を緩和する等、エネルギーレベルを調整するために設ける。
本発明の有機EL素子は、発光層と陰極との間に電子注入層を有し、前記電子注入層は、含窒素環誘導体を主成分として含有することが好ましい。ここで、電子注入層は電子輸送層として機能する層であってもよい。
なお、「主成分として」とは、電子注入層が50質量%以上の含窒素環誘導体を含有していることを意味する。
この含窒素環誘導体としては、例えば、下記式(A)で表される含窒素環金属キレート錯体が好ましい。
ハロゲン原子としては、例えば、フッ素、塩素、臭素、ヨウ素等が挙げられる。また、置換されていてもよいアミノ基の例としては、アルキルアミノ基、アリールアミノ基、アラルキルアミノ基が挙げられる。
アリールアミノ基は-NAr1Ar2と表され、Ar1及びAr2の具体例としては、それぞれ独立に前記非縮合芳香族炭化水素基及び縮合芳香族炭化水素基で説明した基と同様である。Ar1及びAr2の一方は水素原子又は重水素原子であってもよい。
上記式(A)のLは、下記式(A’)又は(A”)で表される基である。
前記式(A’)及び式(A”)のR8~R12及びR13~R27が示す炭素数1~40の炭化水素基としては、前記式(A)中のR2~R7の具体例と同様のものが挙げられる。
また、R8~R12及びR13~R27の互いに隣接する基が環状構造を形成した場合の2価の基としては、テトラメチレン基、ペンタメチレン基、ヘキサメチレン基、ジフェニルメタン-2,2’-ジイル基、ジフェニルエタン-3,3’-ジイル基、ジフェニルプロパン-4,4’-ジイル基等が挙げられる。
Ar20、Ar23及びAr24は、それぞれ置換基を有するもしくは有さない2価の芳香族炭化水素基又は縮合芳香族炭化水素基を示し、Ar23とAr24は、互いに同一でも異なっていてもよい。
2価の芳香族炭化水素基又は縮合芳香族炭化水素基としては、フェニレン基、ナフチレン基、ビフェニレン基、アントラニレン基、ペリレニレン基、ピレニレン基などが挙げられる。そして、これらへの置換基としては炭素数1~10のアルキル基、炭素数1~10のアルコキシ基又はシアノ基等が挙げられる。
HAr-L1-Ar1-Ar2
前記式中、HArは、置換基を有していてもよい炭素数3~40の含窒素複素環基であり、L1は単結合、置換基を有していてもよい炭素数6~40の芳香族炭化水素基又は縮合芳香族炭化水素基又は置換基を有していてもよい炭素数3~40の芳香族複素環基又は縮合芳香族複素環基であり、Ar1は置換基を有していてもよい炭素数6~40の2価の芳香族炭化水素基であり、Ar2は置換基を有していてもよい炭素数6~40の芳香族炭化水素基又は縮合芳香族炭化水素基又は置換基を有していてもよい炭素数3~40の芳香族複素環基又は縮合芳香族複素環基である。
HArは、例えば、下記の群から選択される。
また、R1~R8は、いずれも水素原子又は重水素原子である含窒素複素環誘導体であってもよい。
nは0~4の整数であり、
R1は、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジル基、置換基を有していてもよいキノリル基、置換基を有していてもよい炭素数1~20のアルキル基、または炭素数1~20のアルコキシ基であり、
R2及びR3は、それぞれ独立に、水素原子、重水素原子、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジル基、置換基を有していてもよいキノリル基、置換基を有していてもよい炭素数1~20のアルキル基、または置換基を有していてもよい炭素数1~20のアルコキシ基であり、
Lは、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジニレン基、置換基を有していてもよいキノリニレン基、または置換基を有していてもよいフルオレニレン基であり、
Ar1は、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジニレン基又は置換基を有していてもよいキノリニレン基であり、Ar2は、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジル基、置換基を有していてもよいキノリル基、置換基を有していてもよい炭素数1~20のアルキル基、または置換基を有していてもよい炭素数1~20のアルコキシ基である。
なお、前記式(201)~(203)において、Rは、水素原子、重水素原子、置換基を有していてもよい炭素数6~60の芳香族炭化水素基又は縮合芳香族炭化水素基、置換基を有していてもよいピリジル基、置換基を有していてもよいキノリル基、置換基を有していてもよい炭素数1~20のアルキル基、または置換基を有していてもよい炭素数1~20のアルコキシ基である。
また、電子注入層の構成成分として、含窒素環誘導体の他に無機化合物として、絶縁体又は半導体を使用することが好ましい。電子注入層が絶縁体や半導体で構成されていれば、電流のリークを有効に防止して、電子注入性を向上させることができる。
このような絶縁体又は半導体を使用する場合、その層の好ましい厚みは、0.1nm~15nm程度である。また、本発明における電子注入層は、前述の還元性ドーパントを含有していても好ましい。
正孔注入層又は正孔輸送層(正孔注入輸送層も含む)には、芳香族アミン化合物、例えば、下記一般式(I)で表わされる芳香族アミン誘導体が好適に用いられる。
例えば次のような変更も本発明の好適な変形例である。
エネルギーギャップが広いホスト材料を用いて発光層を形成した場合、ホスト材料のイオン化ポテンシャル(Ip)と正孔注入・輸送層等のIpとの差が大きくなり、発光層への正孔の注入が困難となり、十分な輝度を得るための駆動電圧が上昇するおそれがある。
このような場合、発光層に、正孔注入・輸送性の電荷注入補助剤を含有させることで、発光層への正孔注入を容易にし、駆動電圧を低下させることができる。
具体例としては、トリアゾール誘導体、オキサジアゾール誘導体、イミダゾール誘導体、ポリアリールアルカン誘導体、ピラゾリン誘導体及びピラゾロン誘導体、フェニレンジアミン誘導体、アリールアミン誘導体、アミノ置換カルコン誘導体、オキサゾール誘導体、フルオレノン誘導体、ヒドラゾン誘導体、スチルベン誘導体、シラザン誘導体、ポリシラン系、アニリン系共重合体、導電性高分子オリゴマー(特にチオフェンオリゴマー)等を挙げることができる。
また、ヘキサアザトリフェニレン誘導体等も正孔注入性の材料として好適に用いることができる。
本発明の有機EL素子の各層の形成方法は特に限定されない。従来公知の真空蒸着法、スピンコーティング法等による形成方法を用いることができる。本発明の有機EL素子に用いる、前記式(1)~(4)及び(1’)で表される化合物を含有する有機薄膜層は、真空蒸着法、分子線蒸着法(MBE法)あるいは溶媒に解かした溶液のディッピング法、スピンコーティング法、キャスティング法、バーコート法、ロールコート法等の塗布法による公知の方法で形成することができる。
反応液に水を加えて固体を析出させ、この固体をヘキサン、次いでメタノールで洗浄した。さらに、得られた固体をシリカゲルカラムクロマトグラフィーにて精製し、化合物1-1(2.9g,収率65%)を得た。
FD-MS分析の結果、分子量608に対してm/e=608であった。
FD-MS分析の結果、分子量634に対してm/e=634であった。
FD-MS分析の結果、分子量634に対してm/e=634であった。
FD-MS分析の結果、分子量684に対してm/e=684であった。
反応終了後、直ちにろ過した後、水層を除去した。有機層を硫酸ナトリウムで乾燥させた後、濃縮した。残渣をシリカゲルカラムクロマトグラフィーにて精製し、中間体1-5(31.8g、収率89%)を得た。
FD-MSの分析により、分子量356に対してm/e=356であった。
合成実施例1-2において、中間体1-2のかわりに中間体1-5(2.9g、8.1mmol)を用いた以外は合成実施例1-2と同様に行った。化合物1-5(2.8g、収率56%)を得た。
FD-MS分析の結果、分子量684に対してm/e=684であった。
反応液に水を加えて固体を析出させ、この固体をヘキサン、次いでメタノールで洗浄した。さらに、得られた固体をシリカゲルカラムクロマトグラフィーにて精製し、化合物1-6(3.6g,収率73%)を得た。
FD-MS分析の結果、分子量684に対してm/e=684であった。
次いで、合成実施例1-6において、中間体1-5のかわりに中間体1-7(3.1g,8.1mmol)を用いた以外は合成実施例1-6と同様に行った。化合物1-7(4.4g、収率85%)を得た。
FD-MS分析の結果、分子量710に対してm/e=710であった。
次いで、合成実施例1-6において、中間体1-5のかわりに中間体1-8(2.7g,8.1mmol)を用いた以外は合成実施例1-6と同様に行った。化合物1-8(3.7g、収率77%)を得た。
FD-MS分析の結果、分子量660に対してm/e=660であった。
FD-MS分析の結果、分子量608に対してm/e=608であった。
FD-MS分析の結果、分子量634に対してm/e=634であった。
FD-MS分析の結果、分子量684に対してm/e=684であった。
FD-MS分析の結果、分子量710に対してm/e=710であった。
FD-MS分析の結果、分子量608に対してm/e=608であった。
FD-MS分析の結果、分子量660に対してm/e=660であった。
次いで、ヨウ化銅(5.8g,30mmol)をジメチルホルムアミド(300mL)に溶かし、トランス-1,2-シクロヘキサンジアミン(6.9g,61mmol)を加えた後に、3-ブロモカルバゾール(15g、61mmol)、中間体1-11(20g、61mmol)、リン酸三カリウム(39g,183mmol)を加えて70℃で8時間攪拌した。反応液をろ過し、ろ液を濃縮した。シリカゲルカラムクロマトグラフィーで精製し、中間体1-12(14.9g、収率55%)を得た。
次いで、中間体1-12(14g、31mmol)をTHF(500mL)に溶かし、20℃に冷却後、1.6Mブチルリチウム-ヘキサン溶液(23mL、37mmol)を滴下した。2時間攪拌後、ほう酸トリイソプロピルエステル(11.7g、62mmol)のTHF溶液(50mL)を滴下し、室温で6時間攪拌した。反応液に2N塩酸を加えて30分攪拌した後、有機層を分離し、エバポレーターで溶媒を留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製して中間体1-13(7.9g、収率62%)を得た。
次いで、中間体1-13(7g、17mmol)、2-ブロモカルバゾール(4.2g,17mmol)、テトラキストリフェニルホスフィンパラジウム(0.4g,0.3mmol)、トルエン(25mL)、ジメトキシエタン(25mL)、2M炭酸ナトリウム水溶液(25mL)の順で加えて80℃で8時間加熱攪拌した。反応液の有機層を分離し、エバポレーターで溶媒を留去した。得られた残渣をシリカゲルカラムクロマトグラフィーで精製して中間体1-14(4.8g、収率53%)を得た。
アルゴン雰囲気下、中間体1-15(2.5g,8.1mmol)中間体1-16(3.9g,7.3mmol)、Pd2(dba)3(0.14g,0.15mmol)、P(tBu)3HBF4(0.17g,0.6mmol)、t-ブトキシナトリウム(1.1g,11mmol)、無水キシレン(30mL)の順で加えて8時間加熱還流した。
反応液に水を加えて固体を析出させ、この固体をヘキサン、次いでメタノールで洗浄した。さらに、得られた固体をシリカゲルカラムクロマトグラフィーにて精製し、化合物1-15(4.0g,収率72%)を得た。
FD-MS分析の結果、分子量763に対してm/e=763であった。
25mm×75mm×厚さ1.1mmのITO透明電極付きガラス基板(ジオマティック株式会社製)をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行った。
洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に前記透明電極を覆うようにして下記電子受容性化合物(C-1)を蒸着し、膜厚5nmのC-1膜を成膜した。このC-1膜上に、第1正孔輸送材料として下記芳香族アミン誘導体(X1)を蒸着し、膜厚50nmの第1正孔輸送層を成膜した。第1正孔輸送層の成膜に続けて、第2正孔輸送材料として下記芳香族アミン誘導体(X2)を蒸着し、膜厚60nmの第2正孔輸送層を成膜した。
そして、この発光層成膜に続けて下記化合物(ET2)を膜厚30nmで成膜した。このET1膜は電子輸送層として機能する。
得られた有機EL素子の初期輝度2000cd/m2、室温及びDC定電流駆動での発光効率を測定した結果を第1表に示す。さらに初期輝度5000cd/m2、室温及びDC定電流駆動での発光の半減寿命を測定した結果を第1表に示す。
実施例1-1において、化合物1-1を用いる代わりに第1表に記載の化合物を用いて発光層を形成した以外は実施例1-1と同様にして有機EL素子を作製した。発光効率及び半減寿命の測定結果を第1表に示す。
実施例1-1において、化合物1-1を用いる代わりに化合物1-Dを用いて発光層を形成した以外は実施例1-1と同様にして有機EL素子を作製した。比較例1-4で得た有機EL素子は、燐光発光材料(化合物D3)からの発光は観測されなかった。
化合物1-A及び1-Cを用いた場合、発光層内が正孔過剰となり、電子とのバランスがとれていない。また、化合物1-Cを用いた場合、本発明のビスカルバゾール誘導体に比べて電子輸送性が劣っているために、正孔過剰を解消しきれていない。
上記結果により、本発明の化合物は、比較例で使用した化合物に比べて発光効率と寿命の点で優位であることが明らかである。すなわち、ビスカルバゾール誘導体骨格に適切な縮合環を結合させることがホスト材料の高性能化のためには重要であり、その縮合環としてはフルオランテンやベンゾフェナントレンなどの芳香族縮合環が選ばれることがわかった。
反応液に水を加えて固体を析出させ、この固体をヘキサン、次いでメタノールで洗浄した。さらに、得られた固体をシリカゲルカラムクロマトグラフィーにて精製し、化合物2-1(2.7g,収率62%)を得た。
FD-MS分析の結果、分子量600に対してm/e=600であった。
反応液に水を加えて固体を析出させ、この固体をヘキサン、次いでメタノールで洗浄した。さらに、得られた固体をシリカゲルカラムクロマトグラフィーにて精製し、化合物2-2(3.7g,収率70%)を得た。
FD-MS分析の結果、分子量716に対してm/e=716であった。
反応液に水を加えて固体を析出させ、この固体をヘキサン、次いでメタノールで洗浄した。さらに、得られた固体をシリカゲルカラムクロマトグラフィーにて精製し、化合物2-3(3.15g,収率74%)を得た。
FD-MS分析の結果、分子量584に対してm/e=584であった。
反応液に水を加えて固体を析出させ、この固体をヘキサン、次いでメタノールで洗浄した。さらに、得られた固体をシリカゲルカラムクロマトグラフィーにて精製し、化合物2-4(2.9g,収率65%)を得た。
FD-MS分析の結果、分子量608に対してm/e=608であった。
FD-MS分析の結果、分子量684に対してm/e=684であった。
25mm×75mm×厚さ1.1mmのITO透明電極付きガラス基板(ジオマティック株式会社製)をイソプロピルアルコール中で超音波洗浄を5分間行なった後、UVオゾン洗浄を30分間行った。
洗浄後の透明電極ライン付きガラス基板を真空蒸着装置の基板ホルダーに装着し、まず透明電極ラインが形成されている側の面上に前記透明電極を覆うようにして下記電子受容性化合物(C-1)を蒸着し、膜厚5nmのC-1膜を成膜した。このC-1膜上に、第1正孔輸送材料として下記芳香族アミン誘導体(X1)を蒸着し、膜厚50nmの第1正孔輸送層を成膜した。第1正孔輸送層の成膜に続けて、第2正孔輸送材料として下記芳香族アミン誘導体(X2)を蒸着し、膜厚60nmの第2正孔輸送層を成膜した。
そして、この発光層成膜に続けて下記化合物(ET2)を膜厚30nmで成膜した。このET1膜は電子輸送層として機能する。
得られた有機EL素子の初期輝度2000cd/m2、室温及びDC定電流駆動での発光効率を測定した結果を第2表に示す。さらに初期輝度5000cd/m2、室温及びDC定電流駆動での発光の半減寿命を測定した結果を第1表に示す。
実施例2-1において、化合物2-1を用いる代わりに第2表に記載の化合物を用いて発光層を形成した以外は実施例2-1と同様にして有機EL素子を作製した。
2 基板
3 陽極
4 陰極
5 燐光発光層
6 正孔注入・輸送層
7 電子注入・輸送層
10 有機薄膜層
Claims (20)
- 下記式(1)で表されるビスカルバゾール誘導体。
Y1~Y16は互いに独立してC(R)または窒素原子を表し、Rはそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。
L1及びL2は互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。
但し、A1、A2及びRのうち少なくとも1つは置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のジベンゾトリフェニレニル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のベンゾクリセニル基、置換もしくは無置換のピセニル基、置換もしくは無置換のベンゾ[b]フルオランテニル基、置換もしくは無置換のフェナントレニル基、置換もしくは無置換のビナフチル基、置換もしくは無置換のジベンゾフェナントレニル基、置換もしくは無置換のナフトトリフェニレニル基、置換もしくは無置換のベンゾフルオレニル基又はナフチル基を表す。
また、Y1~Y16が全てC(R)であり、Rが水素であり、Y6とY11が単結合で結合し、L1及びL2が単結合であり、A1がフェナントレニル基の場合、A2はフェニル基、ビフェニリル基又はナフチル基である。さらに、Y1~Y16が全てC(R)であり、Rが水素であり、Y6とY11が単結合で結合し、L1及びL2が単結合であり、A1がナフチル基の場合、A1とA2は互いに異なる。) - 上記式(1)において、A1及びA2の少なくとも一方が、置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のジベンゾトリフェニレニル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のベンゾクリセニル基、置換もしくは無置換のピセニル基、又は置換もしくは無置換のベンゾ[b]フルオランテニル基、置換もしくは無置換のフェナントレニル基、置換もしくは無置換のビナフチル基、置換もしくは無置換のジベンゾフェナントレニル基、置換もしくは無置換のナフトトリフェニレニル基、又は置換もしくは無置換のベンゾフルオレニル基である請求項1に記載のビスカルバゾール誘導体。
- 前記-L1-A1と-L2-A2とが互いに異なる請求項1~4のいずれかに記載のビスカルバゾール誘導体。
- 前記L1及びL2が2価の連結基である請求項1~5のいずれかに記載のビスカルバゾール誘導体。
- 前記A1が、置換もしくは無置換のフルオランテニル基、置換もしくは無置換のトリフェニレニル基、置換もしくは無置換のベンゾフェナントレニル基、置換もしくは無置換のベンゾトリフェニレニル基、置換もしくは無置換のジベンゾトリフェニレニル基、置換もしくは無置換のクリセニル基、置換もしくは無置換のベンゾクリセニル基、置換もしくは無置換のピセニル基、又は置換もしくは無置換のベンゾ[b]フルオランテニル基、置換もしくは無置換のフェナントレニル基、置換もしくは無置換のビナフチル基、置換もしくは無置換のジベンゾフェナントレニル基、置換もしくは無置換のナフトトリフェニレニル基、又は置換もしくは無置換のベンゾフルオレニル基、であり、かつ、A2が、環形成炭素数6~30の置換もしくは無置換の芳香族炭化水素基である請求項1~6のいずれかに記載のビスカルバゾール誘導体。
- 下記式(1a)で表されるビスカルバゾール誘導体。
Y1a~Y16aは互いに独立してC(R)または窒素原子を表し、Rはそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。L1a及びL2aは互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。)
- 請求項1~8のいずれかに記載のビスカルバゾール誘導体からなる有機エレクトロルミネッセンス素子用材料。
- 陰極と陽極の間に発光層を含む複数の有機薄膜層を有し、前記有機薄膜層のうち少なくとも1層が請求項1~9のいずれかに記載のビスカルバゾール誘導体を含む有機エレクトロルミネッセンス素子。
- 陰極と陽極の間に発光層を含む複数の有機薄膜層を有し、前記有機薄膜層のうち少なくとも1層が、下記式(10)で表されるビスカルバゾール誘導体を含む有機エレクトロルミネッセンス素子。
Y1'~Y16'は互いに独立してC(R’)または窒素原子を表し、R’はそれぞれ独立に水素原子、置換基又はカルバゾール骨格に結合する結合手を表す。
L1'及びL2'は互いに独立して単結合、置換もしくは無置換の環形成炭素数6~30の2価の芳香族炭化水素基、又は置換もしくは無置換の環形成炭素数2~30の2価の芳香族複素環基である。) - 前記発光層において前記ビスカルバゾール誘導体をホスト材料として含む請求項10又は11に記載の有機エレクトロルミネッセンス素子。
- 前記発光層が燐光材料を含有する請求項12に記載の有機エレクトロルミネッセンス素子。
- 前記発光層がホスト材料と燐光材料を有し、燐光材料がイリジウム(Ir),オスミウム(Os)、白金(Pt)から選択される金属原子のオルトメタル化錯体である請求項13に記載の有機エレクトロルミネッセンス素子。
- 陰極と発光層の間に電子注入層を有し、該電子注入層が含窒素環誘導体を含む請求項14に記載の有機エレクトロルミネッセンス素子。
- 陰極と発光層の間に電子輸送層を有し、該電子輸送層が前記ビスカルバゾール誘導体を含む請求項15に記載の有機エレクトロルミネッセンス素子。
- 陽極と発光層の間に正孔輸送層を有し、該正孔輸送層が前記ビスカルバゾール誘導体を含む請求項16に記載の有機エレクトロルミネッセンス素子。
- 陰極と有機薄膜層との界面に還元性ドーパントを含有する請求項17に記載の有機エレクトロルミネッセンス素子。
- 請求項10~18のいずれかに記載の有機エレクトロルミネッセンス素子を備えることを特徴とする照明装置。
- 請求項10~19のいずれかに記載の有機エレクトロルミネッセンス素子を備えることを特徴とする表示装置。
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Cited By (41)
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Also Published As
Publication number | Publication date |
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US20160268517A1 (en) | 2016-09-15 |
TW201623576A (zh) | 2016-07-01 |
TWI550059B (zh) | 2016-09-21 |
JP2016138132A (ja) | 2016-08-04 |
KR101588941B1 (ko) | 2016-01-26 |
CN103347857A (zh) | 2013-10-09 |
JP2015180642A (ja) | 2015-10-15 |
CN103347857B (zh) | 2016-08-10 |
TWI538977B (zh) | 2016-06-21 |
TW201235441A (en) | 2012-09-01 |
KR20150061022A (ko) | 2015-06-03 |
JP5745549B2 (ja) | 2015-07-08 |
EP2674418A4 (en) | 2014-07-30 |
EP2674418A1 (en) | 2013-12-18 |
JPWO2012108388A1 (ja) | 2014-07-03 |
US10147888B2 (en) | 2018-12-04 |
US10147889B2 (en) | 2018-12-04 |
KR20140037814A (ko) | 2014-03-27 |
US11271171B2 (en) | 2022-03-08 |
JP5926421B2 (ja) | 2016-05-25 |
CN106117114A (zh) | 2016-11-16 |
KR101720444B1 (ko) | 2017-03-27 |
EP2674418B1 (en) | 2021-01-06 |
US20150249219A1 (en) | 2015-09-03 |
US20140048784A1 (en) | 2014-02-20 |
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