WO2007007464A1 - 含窒素複素環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
含窒素複素環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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- C07D235/02—Heterocyclic compounds containing 1,3-diazole or hydrogenated 1,3-diazole rings, condensed with other rings condensed with carbocyclic rings or ring systems
- C07D235/04—Benzimidazoles; Hydrogenated benzimidazoles
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- C07D401/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings
- C07D401/04—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing two hetero rings directly linked by a ring-member-to-ring-member bond
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- C07D401/14—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, at least one ring being a six-membered ring with only one nitrogen atom containing three or more hetero rings
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- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
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- H05B33/00—Electroluminescent light sources
- H05B33/12—Light sources with substantially two-dimensional radiating surfaces
- H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
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- H10K85/649—Aromatic compounds comprising a hetero atom
- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
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- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/60—Organic compounds having low molecular weight
- H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
- H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
Definitions
- the present invention relates to a novel nitrogen-containing heterocyclic derivative, an organic electoluminescence (EL) device material using the same, and an organic EL device, and particularly, a nitrogen-containing compound useful as a component of the organic EL device.
- the present invention relates to an organic EL device having a low voltage and high luminous efficiency by using a heterocyclic derivative in at least one of the organic compound layers.
- an EL element is composed of a light emitting layer and a pair of counter electrodes sandwiching the layer.
- light emission when an electric field is applied between both electrodes, electrons are injected from the cathode side, and positive holes are injected from the anode side. Furthermore, the electrons recombine with holes in the light emitting layer to generate an excited state, and energy is emitted as light when the excited state returns to the ground state.
- Patent Document 1 discloses an element using a compound having a benzimidazole structure as a light-emitting material, and describes that the element emits light at a luminance of 200 nit at a voltage of 9 V. ing.
- Patent Document 2 describes a compound having a benzimidazole ring and an anthracene skeleton.
- Patent Document 1 US Pat. No. 5,645,948
- Patent Document 2 Japanese Patent Laid-Open No. 2002-38141 Disclosure of the invention
- the present invention has been made to solve the above-mentioned problems, and provides a novel nitrogen-containing heterocyclic derivative useful as a constituent component of an organic EL device.
- the nitrogen-containing heterocyclic derivative is an organic compound.
- An object of the present invention is to realize an organic EL element having a high light emission luminance and high light emission efficiency while being low in voltage by being used in at least one layer.
- the present inventors use a novel nitrogen-containing heterocyclic derivative having a specific structure in at least one organic compound layer of an organic EL device. As a result, it has been found that low voltage, high luminance, and high efficiency of the organic EL element can be achieved, and the present invention has been completed.
- the present invention provides a nitrogen-containing heterocyclic derivative represented by the following general formula (1).
- R 1 ! ⁇ Represents a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, substituted or unsubstituted An unsubstituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 nuclear atoms, a substituted or unsubstituted carbon number 1 ⁇ 50 alkoxy group, substituted or unsubstituted aryloxy group having 5 to 50 carbon atoms, substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms, substituted or unsubstituted alkoxycarbonyl having 1 to 50 carbon atom
- a pair of adjacent substituents of R 3 to R 6 are bonded to each other to form an aromatic ring, and at least one of R 1 to R 6 is a substituent represented by the following general formula (2).
- L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted quinolylene group, or A substituted or unsubstituted fluorenylene group,
- Ar 1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridylene group, or a substituted or unsubstituted quinolinylene group,
- Ar 2 is a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted carbon number of 1 to 50.
- the present invention provides an organic EL element in which an organic thin film layer having at least one light emitting layer or a multi-layer force is sandwiched between a cathode and an anode, and at least one layer force of the organic thin film layer.
- An organic EL device containing a heterocyclic derivative alone or as a component of a mixture is provided.
- the invention's effect [0009]
- the nitrogen-containing heterocyclic derivative of the present invention and the organic EL device using the same are excellent in electron transport property, high light emission efficiency and high light emission efficiency at low voltage.
- the present invention provides a nitrogen-containing heterocyclic derivative represented by the following general formula (1).
- Ri R 6 is a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, substituted or unsubstituted A substituted alkyl group having 1 to 50 carbon atoms, a substituted or unsubstituted cycloalkyl group having 3 to 50 carbon atoms, a substituted or unsubstituted aralkyl group having 6 to 50 nuclear atoms, a substituted or unsubstituted carbon number 1 to 50 alkoxy groups, substituted or unsubstituted aryloxy groups having 5 to 50 carbon atoms, substituted or unsubstituted aryloxy groups having 5 to 50 nuclear atoms, substituted or unsubstituted alkoxycarbonyl groups having 1 to 50 carbon atoms , An amino group substituted with a
- a pair of adjacent substituents of R 3 to R 6 are bonded to each other to form an aromatic ring, and at least one of R 1 to R 6 is a substituent represented by the following general formula (2).
- L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted quinolylene group, or a substituted or unsubstituted group.
- Ar 1 is a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridylene group, or a substituted or unsubstituted quinolinylene group,
- Ar 2 is a hydrogen atom, a substituted or unsubstituted aryl group having 5 to 60 nuclear atoms, a substituted or unsubstituted pyridyl group, a substituted or unsubstituted quinolyl group, a substituted or unsubstituted carbon number of 1 to 50.
- the present invention provides a nitrogen-containing heterocyclic derivative in which the compound represented by the general formula (1) is represented by the following general formula (11a), (11b) or (11c).
- R 7 to R 3 ° are in the general formula (1)! Same as ⁇ ⁇ .
- R 7 to R 14 is a substituent represented by the general formula (2).
- R 15 to R 22 At least one of the substituents represented by the general formula (2), and in the general formula (1 1 c), at least one of R 23 to R 3Q is a substituent represented by the general formula (2).
- the ⁇ aryl group and heterocyclic group include, for example, a phenyl group, a 1 naphthyl group, a 2 naphthyl group, a 1 anthryl group, a 2 anthryl group, a 9 anthryl group, a 1- ⁇ ⁇ nanthryl group, and a 2 phenanthryl.
- a phenyl group, a naphthyl group, a biphenyl group, an anthracenyl group, a phenanthryl group, a pyraryl group, a chrysyl group, a fluoranthuric group, and a fluorine group are preferable.
- Examples of the substituted or unsubstituted alkyl group having 1 to 50 carbon atoms of 1 ⁇ to 1 ⁇ ° include methyl group, ethyl group, propyl group, isopropyl group, n-butyl group, s-butyl group, isobutyl group, and t-butyl group.
- a substituted or unsubstituted alkoxy group having 1 to 50 carbon atoms of 1 ⁇ to 1 ⁇ ° is a group represented by -OY, and examples of Y are the same as those described for the alkyl group. An example is given.
- substituted or unsubstituted aralkyl groups having 1 to 1 ⁇ ° of 6 to 50 nuclear atoms include benzyl group, 1-phenylethyl group, 2-phenylethyl group, 1-phenylisopropyl group, 2—Phenol isopropyl group, Ferro t-butyl group, a Naphthylmethyl group, 1 a Naphthinoreethinore group, 2-a Naftinoreethinole group, 1-a Naphthinoreisopropyl group, 2—a Naphthyl Isopropyl group, 13 naphthylmethyl group, 1- ⁇ naphthylethyl group, 2- ⁇ naphthylethyl group, 1- ⁇ naphthylisopropyl group, 2- ⁇ -naphthylisopropyl group, 1 pyrrolylmethyl group, 2- (1 pyrrolyl) ethyl group
- the substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms is represented by —OY, and examples of Y ′ include the same examples as those described for the aryl group.
- R 1 ! Substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms is represented by -SY ' Examples of Y ′ include the same examples as described for the aryl group.
- the substituted or unsubstituted alkoxycarbo group having 1 to 50 carbon atoms is a group represented by CO OY, and examples of Y include the same examples as those described for the alkyl group.
- Examples of the aryl group in the amino group substituted with a ⁇ to ° substituted or unsubstituted aryl group having 5 to 50 nucleus atoms are the same as those described for the aryl group.
- halogen atom of ⁇ ! ⁇ include a fluorine atom, a chlorine atom, a bromine atom, and an iodine atom.
- a pair of adjacent substituents of R 3 to R 6 are bonded to each other to form an aromatic ring, and the formed ring is preferably a 5-membered ring or a 6-membered ring, particularly a 6-membered ring. Is preferred.
- At least one of Ri to R 6 is a substituent represented by the general formula (2),
- L is a single bond, a substituted or unsubstituted arylene group having 6 to 60 carbon atoms, a substituted or unsubstituted pyridylene group, a substituted or unsubstituted quinolinylene group, or a substituted or unsubstituted fluorylene group. It is.
- the arylene group having 6 to 60 carbon atoms is a divalent substituent formed by removing one hydrogen atom from the substituent described for the aryl group of R 1 ! ⁇ , And preferably a phenol.
- the nitrogen-containing heterocyclic derivative of the present invention is preferably a light-emitting material for an organic EL element, an electron injection material for an organic EL element, or an electron transport material for an organic EL element, which is preferably an organic EL element material. preferable.
- the organic EL device of the present invention is an organic EL device in which an organic thin film layer composed of one or more layers including at least a light emitting layer is sandwiched between a cathode and an anode. At least one layer contains the nitrogen-containing heterocyclic derivative alone or as a component of a mixture.
- the organic thin film layer preferably has a hole transport layer, and the hole transport layer preferably contains the nitrogen-containing heterocyclic derivative of the present invention alone or as a component of a mixture. Further, the hole transport layer preferably contains a nitrogen-containing heterocyclic derivative as a main component.
- the light emitting layer preferably contains a nitrogen-containing heterocyclic derivative, an arylamine compound, and Z or a styrylamine compound.
- arylamine compounds include compounds represented by the following general formula (A), and examples of styrylamine compounds include compounds represented by the following general formula (B).
- Ar represents a fuel, a biphenyl, a terfal, a stilbene, a distyryl.
- Ar and Ar are each a hydrogen atom or 6 carbon atoms.
- Is an aromatic group of ⁇ 20 and Ar to Ar may be substituted.
- p is an integer from 1 to 4.
- aromatic group having 6 to 20 carbon atoms a phenyl group, a naphthyl group, an anthracyl group, a phenanthryl group, a terfel group and the like are preferable.
- Ar to Ar are optionally substituted 5 carbon atoms.
- aryl groups having 5 to 40 nuclear atoms include phenyl, naphthyl, anthracenyl, phenanthryl, pyrenyl, coloninole, biphenyl, terphenyl, pyrrolyl, furanyl, thiophenyl, benzothiophenyl, oxadiazolyl.
- Diphenylanthracenyl, indolyl, carbazolyl, pyridyl, benzoquinolyl, fluoranthenyl, isenaftfluoroolturyl, stilbene and the like are preferable.
- the aryl group having 5 to 40 nucleus atoms may be further substituted with a substituent.
- Examples of the preferable substituent include an alkyl group having 1 to 6 carbon atoms (ethyl group, methyl group, i-propyl group). , N-propyl group, s butyl group, t-butyl group, pentyl group, hexyl group, cyclopentyl group, cyclohexyl group, etc.), C1-C6 alkoxy group (ethoxy group, methoxy group, i-propoxy) Group, n-propoxy group, s butoxy group, t butoxy group, pentoxy group, hexyloxy group, cyclopentoxy group, cyclohexyloxy group, etc.), aryl group having 5 to 40 nuclear atoms, and 5 to 40 nuclear atoms An aryl group substituted with an aryl group, an ester group having an aryl group of 5 to 40 nuclei atoms, an ester group having an alkyl group of 1 to 6 carbon atoms, a
- Anode Z insulating layer Z light emitting layer Z insulating layer Z cathode (10) Anode Z Inorganic semiconductor layer Z insulating layer Z light emitting layer Z insulating layer Z cathode
- the force for which the configuration of (8) is preferably used is not limited to these.
- the nitrogen-containing heterocyclic derivative of the present invention may be used in any organic thin film layer of an organic EL device.
- it can be used in an emission band or an electron transport band, and particularly preferably an electron injection layer, an electron transport layer and a light emission. Used for layers.
- the organic EL device of the present invention is manufactured on a light-transmitting substrate.
- the translucent substrate mentioned here is a substrate that supports the organic EL device, and a smooth substrate with a light transmittance in the visible region of 400 to 700 nm of 50% or more is preferable.
- a glass plate, a polymer plate, etc. are mentioned.
- the glass plate include soda-lime glass, norlium strontium-containing glass, lead glass, aluminosilicate glass, borosilicate glass, norium borosilicate glass, and quartz.
- the polymer plate include polycarbonate, acrylic, polyethylene terephthalate, polyethersulfide, and polysulfone.
- the anode of the organic EL device of the present invention has a function of injecting holes into 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 used in the present invention include indium tin oxide alloy (ITO), acid-tin tin (NE SA), indium-zinc oxide (IZO), gold, silver, platinum, copper, and the like. Can be mentioned.
- the anode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
- the transmittance of the anode for light emission is greater than 10%.
- the sheet resistance of the anode should be several hundred ⁇ preferable.
- the film thickness of the anode is a force depending on the material. Usually, it is selected in the range of 10 nm to l ⁇ m, preferably 10 to 200 nm.
- the light emitting layer of the organic EL device has the following functions (1) to (3).
- Injection function Function that can inject holes from the anode or hole injection layer when an electric field is applied, and can inject electrons from the cathode or electron injection layer
- Transport function Function to move injected charges (electrons and holes) by the force of electric field
- Light emission function A function to provide a field for recombination of electrons and holes and connect this to light emission.However, there is no difference between the ease of hole injection and the ease of electron injection.
- the transport capacity expressed by the mobility of holes and electrons may be large or small, but it is preferable to move one of the charges.
- the light emitting layer is particularly 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.
- a film can be classified from a thin film (accumulated film) formed by the LB method by the difference in aggregated structure and higher-order structure and functional differences resulting from it.
- a binder such as rosin and a material compound are dissolved in a solvent to form a solution, which is then thin-filmed by spin coating or the like.
- the light emitting layer can also be formed by twisting.
- a known light emitting material other than the light emitting material comprising the nitrogen-containing heterocyclic derivative of the present invention may be contained in the light emitting layer as desired, as long as the object of the present invention is not impaired.
- a light emitting layer containing another known light emitting material may be laminated on the light emitting layer containing the light emitting material comprising the nitrogen-containing heterocyclic derivative of the present invention.
- Examples of the light-emitting material or doping material that can be used in the light-emitting layer together with the nitrogen-containing heterocyclic derivative of the present invention include, for example, anthracene, naphthalene, phenanthrene, pyrene, tetracene, coronene, taricene, fluorescein, perylene, phthalate perylene, Naphtha Perylene, Perinone, Liper Mouth Perinone, Naphtha Mouth Perinone, Diphenyl Butadiene, Tetraphenyl Butager , Coumarin, oxadiazole, aldazine, bisbenzoxazoline, bisstyryl, pyrazine, cyclopentagen, quinoline metal complex, aminoquinoline metal complex, benzoquinoline metal complex, imine, diphenylethylene, bulanthracene, diaminocarbazole, pyran, Examples include, but are not limited to, thio
- Ar is a substituted or unsubstituted condensed aromatic group having 10 to 50 nuclear carbon atoms.
- Ar is a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms.
- X is a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, or a substituted or unsubstituted alkyl group having 1 to 50 carbon atoms.
- a, b and c are each an integer of 0-4.
- n is an integer of 1 to 3. When n is 2 or more, the values in [] may be the same or different.
- R 1 -I ⁇ each independently represents a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, or a substituted group.
- Substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms, substituted or unsubstituted alkoxycarbo group having 1 to 50 carbon atoms, substituted or An unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group, and a hydroxyl group.
- Ar and Ar ′ each represent a substituted or unsubstituted aromatic group having 6 to 50 nuclear carbon atoms.
- L and L are each a substituted or unsubstituted phenylene group, a substituted or unsubstituted naphthalene group, a substituted or unsubstituted fluorenylene group, or a substituted or unsubstituted dibenzosilolylene group.
- n is an integer from 1 to 4
- s is an integer from 0 to 2
- t is an integer from 0 to 4.
- L or Ar is bonded to any of the 1-5 positions of pyrene, and L or Ar, is bonded to any of the 6-10 positions of pyrene.
- a 1 and A 2 are each independently a substituted or unsubstituted condensed aromatic ring group having 10 to 20 nuclear carbon atoms.
- Ar 1 and Ar 2 are each independently a hydrogen atom or a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms.
- R 1 -I ⁇ each independently represents a hydrogen atom, a substituted or unsubstituted aromatic ring group having 6 to 50 nuclear carbon atoms, a substituted or unsubstituted aromatic heterocyclic group having 5 to 50 nuclear atoms, or a substituted group.
- Substituted or unsubstituted aryloxy group having 5 to 50 nuclear atoms substituted or unsubstituted aryloxy group having 5 to 50 nucleus atoms, substituted or unsubstituted alkoxycarbo group having 1 to 50 carbon atoms, substituted or An unsubstituted silyl group, a carboxyl group, a halogen atom, a cyano group, a nitro group or a hydroxyl group.
- Ar 2 , R 9 and R 1Q may be plural or adjacent to each other to form a saturated or unsaturated cyclic structure.
- 1 ⁇ to 1 ⁇ ° are independently a hydrogen atom, an alkyl group, a cycloalkyl group, an optionally substituted aryl group, an alkoxyl group, an aryloxy group, an alkylamino group, an alkyl group
- An arylamino group or an optionally substituted heterocyclic group, a and b each represent an integer of 1 to 5, and when they are 2 or more, R 1 or R 2 are each be the same or different Yogumata R1 together or R2 may be bonded to each other to form a ring
- R 3 and R 4, R 5 and R 6, R 7 and R 8, R 9 and R 1 (> may be bonded to each other to form a ring.
- L 1 is a single bond, —O—, 1 S—, — N (R) — (R is an alkyl group or an optionally substituted aryl Group), an alkylene group or an arylene group.
- R u to! ⁇ are each independently a hydrogen atom, an alkyl group, a cycloalkyl group, an aryl group, an alkoxyl group, an aryloxy group, an alkylamino group, an arylamino group, or Cd, e and f each represent an integer from 1 to 5, R 11 or more, R 12 , R 16, or R 17 may be the same or different from each other. R 11 , R 12 , R 16, or R 17 They may be bonded to each other to form a ring, or R 13 and R 14 , R 18 and R 19 may be bonded to each other to form a ring.
- L 2 represents a single bond, —O—, 1 S—, —N (R) — (where R is an alkyl group or an optionally substituted aryl group), an alkylene group or an arylene group. )
- a 5 to A 8 each independently represents a substituted or unsubstituted biphenyl group or a substituted or unsubstituted naphthyl group.
- R 21 to R 23 are each independently a hydrogen atom, an alkyl group having 1 to 6 carbon atoms, a cycloalkyl group having 3 to 6 carbon atoms, An alkoxyl group having 1 to 6 carbon atoms, an aryloxy group having 5 to 18 carbon atoms, an aralkyloxy group having 7 to 18 carbon atoms, an arylamino group having 5 to 16 carbon atoms, a nitro group, a cyano group, and an ester group having 1 to 6 carbon atoms. Or a halogen atom, and at least one of A 9 to A 14 is a group having three or more condensed aromatic rings. is there. )
- R and R are a hydrogen atom, a substituted or unsubstituted alkyl group, a substituted or
- R and R bonded to may be the same or different.
- R and R are hydrogen
- R and R bonded to the same fluorene group may be the same or different.
- 3 4 1 and Ar are substituted or unsubstituted condensed polycyclic aromatics with a total of 3 or more benzene rings
- n an integer of 1 to 10.
- anthracene derivatives are preferable, monoanthracene derivatives are more preferable, and asymmetric anthracene is particularly preferable.
- a phosphorescent compound can also be used as the dopant light-emitting material.
- a compound containing a force rubazole ring as a host material is preferable.
- the dopant is a compound capable of emitting triplet exciton force, and is not particularly limited as long as it also emits triplet exciton force, but also Ir, Ru, Pd, Pt, Os and Re force It is preferably a metal complex containing at least one metal whose group power is also selected.
- a host suitable for phosphorescence emission with a compound power containing a strong rubazole ring is a compound having the function of emitting a phosphorescent compound as a result of energy transfer from its excited state to the phosphorescent compound. is there.
- the host compound is not particularly limited as long as it is a compound that can transfer the exciton energy to the phosphorescent compound, and can be appropriately selected according to the purpose. It may have an arbitrary heterocyclic ring in addition to the force rubazole ring.
- host compounds include force rubazole derivatives, triazole derivatives, oxazole derivatives, oxaziazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, furan diamine derivatives, arylamine derivatives , Amino-substituted chalcone derivatives, styrylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, silazane derivatives, aromatic tertiary amine compounds, styrylamine compounds, aromatic dimethylidene compounds, porphyrin compounds, anthraquinodis Methane derivatives, anthrone derivatives, diphenylquinone derivatives, thiobilane dioxide derivatives, carpositimide derivatives, fluorenylidenemethane derivatives, distyrylvirazine derivatives, naphthalene derivatives Heterocycl
- a phosphorescent dopant is a compound capable of emitting triplet exciton power.
- the triplet exciton force is not particularly limited as long as it emits light, but it is preferably a metal complex containing at least one metal selected from the group force Ir, Ru, Pd, Pt, Os and Re force, and is preferably a porphyrin metal complex or orthometal ion. ⁇ Metal complexes are preferred.
- the porphyrin metal complex is preferably a porphyrin platinum complex.
- the phosphorescent compound may be used alone or in combination of two or more.
- ligands that form ortho-metal complexes
- preferred ligands include 2 phenyl pyridine derivatives, 7, 8 benzoquinoline derivatives, and 2- (2-Che) pyridine derivatives. , 2- (1 naphthyl) pyridine derivatives, 2-phenol-quinoline derivatives, and the like. These derivatives may have a substituent as necessary. In particular, it is preferred as a blue dopant with a fluoride or trifluoromethyl group introduced. Further, it may have a ligand other than the above ligands such as acetylylacetonate and picric acid as an auxiliary ligand.
- the content of the phosphorescent dopant in the light-emitting layer is not particularly limited, and can be appropriately selected according to the purpose.
- the content is 0.1 to 70% by mass, and 1 to 30% by mass. preferable. If the phosphorescent emissive compound content is less than 0.1% by mass, the light emission is weak and the content effect is not fully exhibited. If the content exceeds 70% by mass, concentration quenching occurs. The so-called phenomenon becomes remarkable and the device performance deteriorates.
- the light emitting layer may contain a hole transport material, an electron transport material, and a polymer binder as necessary.
- the thickness of the light emitting layer is preferably 5 to 50 nm, more preferably 7 to 50 nm, and most preferably 10 to 50 nm. If the thickness is less than 5 nm, it is difficult to form a light emitting layer, and it may be difficult to adjust the chromaticity. If it exceeds 50 nm, the driving voltage may increase.
- the hole injection 'transport layer is a layer that helps injecting holes into the light emitting layer and transports it to the light emitting region, and has a high ion mobility with a high hole mobility, usually less than 5.5 eV.
- a hole injection / transport layer a material that transports holes to the light-emitting layer with a lower electric field strength is preferable.
- the mobility force of holes for example, 10 4 ⁇ : When an electric field of LO Zcm is applied, At least 10 4 cm 2 ZV ⁇ sec is preferred! /.
- the nitrogen-containing heterocyclic derivative of the present invention When the nitrogen-containing heterocyclic derivative of the present invention is used in the hole transport zone, the nitrogen-containing heterocyclic derivative of the present invention alone is used by mixing with other materials that may form a hole injection or transport layer. Also good.
- the material for forming the hole injection / transport layer by mixing with the nitrogen-containing heterocyclic derivative of the present invention is not particularly limited as long as it has the above-mentioned preferred properties. Any of those commonly used as materials and known materials used for hole injection and transport layers of organic EL devices can be selected and used.
- silazane derivatives US Pat. No. 4,950,950
- polysilanes JP-A-2-204996
- aniline-based copolymers JP-A-2-282263 Gazette
- Japanese Unexamined Patent Publication No. 1-211399 examples thereof include conductive polymer oligomers (particularly thiophene oligomers).
- the above-described materials can be used as the material for the hole injection and transport layer.
- Volphiline compounds (disclosed in JP-A-63-29556965), aromatic tertiary amine compounds and styryl.
- Amine compound US Pat. No.
- inorganic compounds such as p-type Si and p-type SiC can be used as the material for the hole injection / transport layer in addition to the above-mentioned aromatic dimethylidin-based compounds shown as the material for the light emitting layer.
- the hole injection 'transport layer is formed by thinning the nitrogen-containing heterocyclic derivative of the present invention by a known method such as a vacuum deposition method, a spin coating method, a casting method, or an LB method. Can do.
- the thickness of the hole injection 'transport layer is not particularly limited, but is usually 5 ⁇ ! ⁇ 5 m.
- This hole injecting / transporting layer may be composed of one or more layers of the above-mentioned materials as long as it contains the nitrogen-containing heterocyclic derivative of the present invention in the hole transporting zone.
- the hole injection / transport layer may be a laminate of a hole injection / transport layer made of a different kind of compound from the hole injection / transport layer.
- a hole injection or electron injection organic semiconductor layer provided as a layer to help Moyogu 10- 1Q SZcm more of the conductivity of the light-emitting layer.
- the material for such an organic semiconductor layer include thiophene oligomers, conductive oligomers such as allylamin oligomers disclosed in JP-A-8-193191, and conductive properties such as allylamin dendrimers. Dendrimers and the like can be used.
- Electron injection 'transport layer (electron transport zone)
- the electron injection layer 'transport layer is a layer that assists the injection of electrons into the light emitting layer and transports it to the light emitting region, and has a large electron mobility and usually a high electron affinity of 2.5 eV or more.
- a material that transports electrons to the light emitting layer with a lower electric field strength is preferable.
- an electron mobility force of, for example, 10 4 to: at least when an electric field of LO Zcm is applied 10 6 cm 2 / V 'sec is preferred! /.
- the electron-injecting / transporting layer may be formed of the nitrogen-containing heterocyclic derivative of the present invention alone or may be mixed with other materials.
- the material for mixing with the nitrogen-containing heterocyclic derivative of the present invention to form an electron injecting / transporting layer is not particularly limited as long as it has the above-mentioned preferable properties. Any one of commonly used ones and known ones used for the electron injection / transport layer of organic EL devices can be selected and used.
- the adhesion improving layer is a layer made of a material that has a particularly good adhesion to the cathode in the electron injection layer.
- the compound of the present invention is preferably used as an electron injection layer, a transport layer, and an adhesion improving layer.
- a preferred form of the organic EL device of the present invention is a device containing a reducing dopant in an electron transporting region or an interface region between the cathode and the organic layer.
- an organic EL device containing a reducing dopant in the compound of the present invention is preferable.
- the reducing dopant is defined as a substance capable of reducing an electron transporting compound. Accordingly, various materials can be used as long as they have a certain reducibility, such as alkali metals, alkaline earth metals, rare earth metals, alkali metal oxides, alkali metal halides, alkaline earths.
- preferable reducing dopants include Na (work function: 2.36 eV), K (work function: 2.28 eV), Rb (work function: 2.16 eV), and Cs (work function: 1).
- 95eV) Force Group Force At least one selected alkali metal, Ca (work function: 2.9 eV;), Sr (work function: 2.0 to 2.5 eV), and Ba (work function: 2.
- a more preferable reducing dopant is at least one alkali metal selected from the group force consisting of K, Rb and Cs, and more preferably, Rb or Cs, the most preferred is Cs.
- alkali metals in particular, can improve the emission brightness and extend the life of organic EL devices by adding a relatively small amount to the electron injection region where the reducing ability is high.
- a reducing dopant having a work function of 2.9 eV or less a combination of two or more alkali metals is also preferable. Particularly, combinations containing Cs, for example, Cs and Na, Cs and K, and Cs. A combination of Rb or Cs, Na and ⁇ is preferred. By including Cs in combination, the reducing ability can be efficiently exhibited, and by adding it to the electron injection region, the emission luminance of the organic EL element can be improved and the lifetime can be extended.
- an electron injection layer composed of an insulator or a semiconductor may be further provided between the cathode and the organic layer.
- an insulator at least one metal compound selected from the group consisting of an alkali metal chalcogenide, an alkaline earth metal chalcogenide, an alkali metal halide and an alkaline earth metal halide is used. Is preferred. 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.
- preferred alkali metal chalcogenides include, for example, Li 0, K 0, Na S, Na Se, and Na 2 O,
- Preferred alkaline earth metal chalcogenides include, for example, CaO, BaO, SrO, BeO, BaS, and CaSe.
- Preferred alkali metal halides include, for example, LiF, NaF, KF, LiCl, KC1, and NaCl.
- Preferred alkaline earth metal halides include, for example, CaF, BaF, SrF, MgF, and the like.
- Examples include fluorides such as 2 2 2 2 and BeF, and halides other than fluorides.
- the electron transport layer an oxide containing at least one element of Ba, Ca, Sr, Yb, Al, Ga, In, Li, Na, Cd, Mg, Si, Ta, Sb and Zn , Nitrides or oxynitrides, or a combination of two or more thereof.
- the inorganic compound constituting the electron transport layer is preferably a microcrystalline or amorphous insulating thin film. If the electron transport layer is composed of these insulating thin films, a more uniform thin film is formed, so that pixel defects such as dark spots can be reduced.
- examples of such inorganic compounds include the alkali metal chalcogenides, alkaline earth metal chalcogenides, alkali metal halides, and alkaline earth metal halides described above.
- the cathode in order to inject electrons into the electron injecting / transporting layer or the light emitting layer, a material having a small work function (4 eV or less) metal, an alloy, an electrically conductive compound, and a mixture thereof is used.
- electrode materials include sodium, sodium 'potassium alloy, magnesium, lithium, magnesium' silver alloy, aluminum / acid aluminum, aluminum 'lithium alloy, indium, and rare earth metals. It is done.
- This cathode can be produced by forming a thin film of these electrode materials by a method such as vapor deposition or sputtering.
- the transmittance for the light emission of the cathode is preferably larger than 10%.
- the sheet resistance as a cathode is several hundred ⁇ or less.
- the preferred film thickness is usually ⁇ ! To 1 m, preferably 50 to 200 nm.
- organic EL devices apply an electric field to ultra-thin films, pixel defects are likely to occur due to leaks and shorts. In order to prevent this, it is preferable to insert an insulating thin film layer between the pair of electrodes.
- Examples of materials used for the insulating layer include aluminum oxide, lithium fluoride, lithium oxide, cesium fluoride, cesium oxide, magnesium oxide, magnesium fluoride, calcium oxide, calcium fluoride, aluminum nitride, and titanium oxide. , Silicon oxide, oxide germanium, silicon nitride, boron nitride, molybdenum oxide, ruthenium oxide, vanadium oxide, and the like, and a mixture or laminate thereof may be used.
- anode By forming the anode, the light-emitting layer, the hole injection 'transport layer, and the electron injection' transport layer as necessary, and the cathode by forming the anode and the light-emitting layer, if necessary, by the materials and formation methods exemplified above, and further forming the cathode An element can be manufactured. Also, from the cathode to the anode, there is a reverse order. Machine EL elements can also be produced.
- an organic EL device having a configuration in which an anode, a hole injection layer, a Z light emitting layer, a Z electron injection layer, and a Z cathode are sequentially provided on a light transmitting substrate will be described.
- a thin film made of an anode material is formed on a suitable translucent substrate by a method such as vapor deposition or sputtering so as to have a film thickness of 1 ⁇ m or less, preferably in the range of 10 to 200 nm, to produce an anode.
- a hole injection layer is provided on the anode.
- the hole injection layer can be formed by a vacuum deposition method, a spin coating method, a casting method, an LB method, or the like, but a homogeneous film can be obtained immediately and pinholes are generated. It is preferable to form by a vacuum vapor deposition method.
- the deposition conditions vary depending on the compound used (material of the hole injection layer), the crystal structure and recombination structure of the target hole injection layer, etc.
- a light-emitting layer in which a light-emitting layer is provided on a hole injection layer is performed by using a desired organic light-emitting material to form a thin film of an organic light-emitting material by a method such as vacuum deposition, sputtering, spin coating, or casting. It is preferable to form the film by vacuum evaporation from the standpoints that it can be formed by rubbing, but a homogeneous film can be obtained immediately and pinholes are not easily generated.
- the deposition conditions vary depending on the compound used, but can generally be selected from the same condition range as the hole injection layer.
- an electron injection layer is provided on the light emitting layer.
- a vacuum deposition method because a uniform film is required.
- the vapor deposition conditions can be selected from the same condition ranges as those for the hole injection layer and the light emitting layer.
- the nitrogen-containing heterocyclic derivative of the present invention varies depending on which layer in the emission band or the hole transport band, but when using the vacuum evaporation method, co-evaporation with other materials should be performed. Can do. Moreover, when using a spin coat method, it can be contained by mixing with other materials.
- a cathode can be stacked to obtain an organic EL device.
- the cathode also has a metallic force, and vapor deposition and sputtering can be used. Shi Force Vacuum deposition is preferred in order to protect the underlying organic layer from damages during film formation. It is preferable to fabricate this organic EL device from the anode to the cathode consistently by a single vacuum.
- the method for forming each layer of the organic EL device 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 compound represented by the general formula (1) used in the organic EL device of the present invention is a vacuum deposition method, a molecular beam deposition method (MBE method) or a dating method of a solution dissolved in a solvent, It can be formed by a known method such as 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, but in general, if the film thickness is too thin, defects such as pinholes are generated. Usually, the range of several nm to 1 ⁇ m is preferable because of worsening.
- a direct current voltage When a direct current voltage is applied to the organic EL element, light emission can be observed by applying a voltage of 5 to 40 V with the anode set to + and the cathode set to one polarity. In addition, even when a voltage is applied with the opposite polarity, no current flows and no light emission occurs. Furthermore, when AC voltage is applied, uniform light emission is observed only when the anode is + and the cathode is of the same polarity.
- the alternating current waveform to be applied may be arbitrary.
- 2-Toro 4-bromo 1-phenolaminonaphthalene (5.0 g, 0.015 mol) was dissolved in 50 mL of tetrahydrofuran and stirred at room temperature under an argon atmosphere, and 13 g of sodium hydrosulfite ( 0.075 mol) / water 40 mL solution was added dropwise. Further, 5 mL of methanol was added and stirred for 1 hour. Next, 40 mL of ethyl acetate was added, and a solution of sodium hydrogen carbonate 2.5 g (0.030 mol) Z water 20 mL was added.
- a 25 mm X 75 mm X 1.1 mm thick glass substrate with ITO transparent electrode (anode) (Zomatic) was ultrasonically cleaned in isopropyl alcohol for 5 minutes, followed by UV ozone cleaning for 30 minutes.
- the glass substrate with the transparent electrode line after cleaning is mounted on the substrate holder of the vacuum evaporation system.
- the transparent electrode is covered on the surface on which the transparent electrode line is formed.
- 1-bis (N, N, 1-diphenyl 4-aminophenol) — N, N-diphenyl— 4, 4, — diamino-1, 1, -biphenyl membrane (hereinafter referred to as “TPD23 2 membrane”) Is abbreviated as a film).
- This TPD232 film functions as a hole injection layer.
- NPD film 4,4, -bis [N— (1-naphthyl) -N-phenolamino] bi-film film (hereinafter “NPD film”) with a thickness of 20 nm is formed on the TPD232 film. Abbreviated as “)”. This NPD film functions as a hole transport layer.
- the following anthracene derivative A1 and styrylamine derivative S1 having a film thickness of 40 nm were formed at a film thickness ratio of 40: 2 to form a blue light emitting layer.
- Example 2 the compound (1) was deposited as an electron transport layer with a thickness of 20 nm by vapor deposition. Thereafter, LiF was deposited to a thickness of 1 nm. On this LiF film, 150 nm of metal A1 was deposited to form a metal cathode to form an organic EL light emitting device. [0074]
- Example 2 the compound (1) was deposited as an electron transport layer with a thickness of 20 nm by vapor deposition. Thereafter, LiF was deposited to a thickness of 1 nm. On this LiF film, 150 nm of metal A1 was deposited to form a metal cathode to form an organic EL light emitting device.
- An organic EL device was produced in the same manner as in Example 1, except that compound (2) was used instead of compound (1).
- Example 1 an organic EL device was produced in the same manner except that the following compound A described in International Publication WO 2004/080975 A1 was used instead of the compound (1).
- Example 1 an organic EL device was produced in the same manner except that the following compound B described in International Publication WO 2004/080975 A1 was used instead of the compound (1).
- An organic EL device was produced in the same manner as in Example 1 except that Alq (8-hydroxyquinoline aluminum complex) was used instead of the compound (1).
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Abstract
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Priority Applications (2)
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US11/995,407 US20090278115A1 (en) | 2005-07-11 | 2006-05-10 | Nitrogen-containing heterocyclic derivative and organic electroluminescence element using the same |
JP2007524530A JPWO2007007464A1 (ja) | 2005-07-11 | 2006-05-10 | 含窒素複素環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 |
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US (1) | US20090278115A1 (ja) |
JP (1) | JPWO2007007464A1 (ja) |
KR (1) | KR20080028424A (ja) |
CN (1) | CN101218208A (ja) |
TW (1) | TW200704749A (ja) |
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US8563746B2 (en) | 2008-10-29 | 2013-10-22 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
US8329914B2 (en) | 2008-10-31 | 2012-12-11 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
CN102482575A (zh) * | 2009-09-10 | 2012-05-30 | 株式会社Lg化学 | 新的杂环衍生物及使用其的有机电致发光器件 |
CN102482575B (zh) * | 2009-09-10 | 2015-01-21 | 株式会社Lg化学 | 新的杂环衍生物及使用其的有机电致发光器件 |
US8895596B2 (en) | 2010-02-25 | 2014-11-25 | Merck Sharp & Dohme Corp | Cyclic benzimidazole derivatives useful as anti-diabetic agents |
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TW200704749A (en) | 2007-02-01 |
US20090278115A1 (en) | 2009-11-12 |
KR20080028424A (ko) | 2008-03-31 |
JPWO2007007464A1 (ja) | 2009-01-29 |
CN101218208A (zh) | 2008-07-09 |
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