WO2012132501A1 - 硬化性組成物、硬化物及びそれを用いた有機電界発光素子 - Google Patents
硬化性組成物、硬化物及びそれを用いた有機電界発光素子 Download PDFInfo
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- WO2012132501A1 WO2012132501A1 PCT/JP2012/051060 JP2012051060W WO2012132501A1 WO 2012132501 A1 WO2012132501 A1 WO 2012132501A1 JP 2012051060 W JP2012051060 W JP 2012051060W WO 2012132501 A1 WO2012132501 A1 WO 2012132501A1
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- CEYMUUWQMPULGD-UHFFFAOYSA-N C=Cc(cc1)ccc1-[n]1c(cc(c2ccccc2[n]2-c3ccc(C=C)cc3)c2c2)c2c2c1cccc2 Chemical compound C=Cc(cc1)ccc1-[n]1c(cc(c2ccccc2[n]2-c3ccc(C=C)cc3)c2c2)c2c2c1cccc2 CEYMUUWQMPULGD-UHFFFAOYSA-N 0.000 description 1
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- H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
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- C08G59/00—Polycondensates containing more than one epoxy group per molecule; Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups
- C08G59/18—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing
- C08G59/20—Macromolecules obtained by polymerising compounds containing more than one epoxy group per molecule using curing agents or catalysts which react with the epoxy groups ; e.g. general methods of curing characterised by the epoxy compounds used
- C08G59/22—Di-epoxy compounds
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- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
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- H05B33/00—Electroluminescent light sources
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- H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
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Definitions
- the present invention relates to a curable composition containing an indolocarbazole skeleton compound having two polymerizable groups, a cured product, and an organic electroluminescent device using the same.
- electroluminescent elements include inorganic electroluminescent elements using inorganic compounds and organic electroluminescent elements using organic compounds.
- organic light emitting devices with low voltage and high luminance can be obtained. Research on practical application of electroluminescent devices is actively conducted.
- the structure of the organic electroluminescence device is that a hole injection layer is formed on a glass plate on which a thin film of an anode material such as indium-tin oxide (ITO) is deposited, and an organic thin film layer such as a light emitting layer is further formed thereon.
- a device is formed by forming a thin film of a cathode material, and there is an element in which a hole transport layer and an electron transport layer are appropriately provided in this basic structure.
- the layer structure of the organic electroluminescent device is, for example, anode / hole injection layer / light emitting layer / electron transport layer / cathode, anode / hole injection layer / hole transport layer / light emitting layer / electron transport layer / cathode, etc. is there.
- Hole transport materials used for the hole transport layer of the organic electroluminescence device are roughly classified into low molecular weight hole transport materials and high molecular weight hole transport materials.
- a vacuum deposition method is mainly used.
- various materials having different functions can be easily multilayered.
- high-performance organic electroluminescent elements can be formed, it is difficult to uniformly control the film thickness and paint separately due to the large screen and high definition of the panel. There is a problem of becoming higher.
- a solution coating method such as a spin coating method, a printing method, an ink jet method or the like is used. Although this method is easy to enlarge and is excellent in mass production, mixing between layers is likely to occur, functional separation by lamination is not possible, and there are necessary characteristics different from dry methods such as solubility in solvents. In addition, there is a problem that charge injection materials and charge transport materials that can be used in the wet method are limited.
- Patent Document 1 reports an acrylic compound or a cured product thereof
- Patent Document 2 reports a cured product using an NPD having a vinyl group.
- organic electroluminescent devices using these compounds although functional separation is achieved by stacking, electron resistance and charge transport performance are not sufficient, and sufficient characteristics have not been obtained.
- Patent Document 3 discloses a conjugated polymer bonded at the 6th and 12th positions of indolocarbazole
- Patent Document 4 discloses a conjugated polymer having N-substituted indolocarbazole as the main skeleton.
- the present invention has been made in view of the above problems, and has a curable composition containing an indolocarbazole skeleton compound having two polymerizable groups for an organic electroluminescent device applicable to a wet process with high luminous efficiency. It aims at providing a thing and its hardened
- cured material. Another object of the present invention is to provide an organic electroluminescence device using the curable composition or a cured product thereof used for a lighting device, an image display device, a backlight for a display device, and the like.
- the present inventor has intensively studied and contains other materials by using a curable composition containing an indolocarbazole skeleton compound having two polymerizable groups and a cured product. It has been found that the organic layer can be laminated on the upper layer by coating, and the light emission performance is improved, and the present invention has been completed.
- the present invention has a curable composition containing an indolocarbazole skeleton compound having two polymerizable groups, a cured product, and an organic layer between an anode layer and a cathode layer laminated on a substrate.
- an organic electroluminescent element it is related with the organic electroluminescent element in which at least one layer is a layer containing this curable composition or hardened
- the present invention when the total number of moles of the compound represented by the general formula (1) and the compound represented by the general formula (2) is 100, the compound represented by the general formula (1) is 5 to 100 mol%, The present invention relates to a curable composition containing 0 to 95 mol% of the compound represented by the general formula (2).
- ring A represents a heterocycle represented by the formula (1a) fused with an adjacent ring at an arbitrary position
- R represents a hydrogen atom, a C 1 to C 20 alkyl group, or a C 1 to C 20 alkoxy group.
- Y 1 represents a single bond or a divalent group, and may be the same or different.
- C 1 -C 20 alkylene group, C 6 -C 30 arylene group, C 3 -C 30 heteroarylene group, CO, COO or O may be the same or different.
- W 1 is a polymerizable group and may be the same or different.
- Z represents a C 6 -C 30 aryl group, a C 3 -C 30 heteroaryl group or a C 12 -C 60 diarylamino group.
- Y 2 represents a single bond or a divalent group.
- W 2 is a polymerizable group.
- Z, R, Y 1 and Y 2 do not have a condensed ring structure of 5 or more rings.
- Preferable examples of the compound represented by the general formula (1) include compounds represented by the following formula (3) or (4).
- formula (3) or (4) Y 1 and W 1 are the same as those in general formula (1), and R 1 is the same as R in general formula (1).
- Z in the general formula (2) preferably has at least one group represented by the following formula (9), (10) or (11) inside.
- Ar 1 and Ar 2 independently represent a C 6 to C 30 aryl group or a C 3 to C 30 heteroaryl group, and Ar 1 , Ar 2 and N form a condensed ring. It doesn't matter. However, Ar 1 and Ar 2 do not have 5 or more condensed ring structures.
- R 2 is a hydrogen atom, a C 1 to C 20 alkyl group, a C 1 to C 20 alkoxy group, a C 6 to C 30 aryl group, or a C 6 to C 30 aryl group.
- Oxy group, C 7 -C 36 arylalkyl group, C 7 -C 36 arylalkyloxy group, C 3 -C 30 heteroaryl group, C 3 -C 30 heteroaryloxy group, C 4 -C 36 A heteroarylalkyl group, a C 4 -C 36 heteroarylalkyloxy group or a C 3 -C 30 cycloalkyl group, which may be the same or different.
- R 2 does not have a condensed ring structure having 5 or more rings.
- the polymerizable groups W 1 and W 2 in the general formulas (1), (1a) and (2) are preferably a radical polymerizable group or a cationic polymerizable group.
- the polymerizable groups W 1 and W 2 are preferably at least one group independently selected from a vinyl group, a vinyl group substituted with an alkyl group having 1 to 6 carbon atoms, an epoxy group, and an oxetanyl group.
- W 1 and W 2 are vinyl groups selected from a vinyl group and a substituted vinyl group, and the compound represented by formula (1) is a vinyl group. It is preferable that the compound represented by General Formula (2) has one vinyl group.
- the present invention also relates to a cured product obtained by polymerizing and curing the curable composition.
- the said curable composition may contain the compound represented by General formula (1) independently, and includes both the compound represented by General formula (1), and the compound represented by General formula (2). It may be.
- the cured product obtained by polymerizing and curing the curable composition may be a homopolymer of the compound represented by the general formula (1) and the compound represented by the general formula (2). It may be a polymer.
- the present invention relates to an organic electroluminescent device having an organic layer between an anode layer and a cathode layer laminated on a substrate, wherein the organic electric field contains the cured product in at least one layer of the organic layer.
- the present invention relates to a light emitting element.
- a hole transport layer is mentioned as an organic layer containing the said hardened
- the curable composition of the present invention and the cured product thereof contain an indolocarbazole skeleton having two polymerizable groups capable of imparting excellent charge transport ability, particularly hole transport ability.
- the curable composition of the present invention contains an indolocarbazole skeleton compound having two polymerizable groups represented by the general formula (1).
- the indolocarbazole skeleton is formed by taking two Hs at two N positions from a five-ring condensed ring compound in which an indole ring and a carbazole ring are condensed. Since this skeleton has a plurality of condensable positions of the indole ring and the carbazole ring, when the two N-position substituents are different, the six structural isomers of the following formulas (A) to (F) A group may be taken, but any structural isomer may be used.
- (C) and (F) have the same structure, and there are five isomers.
- the indolocarbazole skeleton can have a substituent as long as the effects of the present invention are not inhibited.
- the ring A represents a heterocyclic ring represented by the formula (1a) that is condensed with an adjacent ring at an arbitrary position.
- the structure has any one of the above formulas (A) to (F).
- R is a hydrogen atom, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 30 aryl group, a C 6 -C 30 aryloxy group, C 7 -C 36 arylalkyl group, C 7 -C 36 arylalkyloxy group, C 3 -C 30 heteroaryl group, C 3 -C 30 heteroaryloxy group, C 4 -C 36 heteroaryl Represents an alkyl group, a C 4 -C 36 heteroarylalkyloxy group or a C 3 -C 30 cycloalkyl group, which may be the same or different;
- a hydrogen atom, a C 1 -C 20 alkyl group, a C 1 -C 20 alkoxy group, a C 6 -C 30 aryl group, a C 3 -C 30 heteroaryl group, or a C 3 -C 30 cyclo group is preferred.
- alkyl group more preferably a hydrogen atom, a C 1 -C 8 alkyl group, a C 1 -C 8 alkoxy group, a C 6 -C 18 aryl group, a C 3 -C 18 heteroaryl group, or a C 1 A 3 to C 12 cycloalkyl group.
- These groups may further have a substituent as long as the performance is not adversely affected.
- R does not have a condensed ring structure of 5 or more rings.
- alkyl group examples include a methyl group, an ethyl group, a propyl group, a butyl group, a pentyl group, a hexyl group, a heptyl group, an octyl group, a nonyl group, and a decyl group, preferably a methyl group, an ethyl group, and a propyl group.
- an alkyl group having 1 to 8 carbon atoms such as a group, a butyl group, a pentyl group, a hexyl group, a heptyl group, or an octyl group.
- the alkyl chain may be linear or branched.
- alkoxy group examples include methyloxy group, ethyloxy group, propyloxy group, butyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, octyloxy group, nonyloxy group, decyloxy group, preferably methyl
- alkyloxy groups having 1 to 8 carbon atoms such as oxy group, ethyloxy group, propyloxy group, butyloxy group, pentyloxy group, hexyloxy group, heptyloxy group, and octyloxy group.
- the alkyl chain may be linear or branched.
- aryl group and heteroaryl group include benzene, pentalene, indene, naphthalene, azulene, heptalene, octalene, indacene, acenaphthylene, phenalene, phenanthrene, anthracene, tridene, fluoranthene, acephenanthrylene, acanthrylene, and triphenylene.
- the number to be linked is preferably 2 to 10, more preferably 2 to 7, and the linked aromatic rings may be the same. It may be different. In that case, the position of the bond is not limited, and it may be the ring at the end of the linked aromatic ring or the ring at the center.
- the aromatic ring is a generic term for an aromatic hydrocarbon ring and an aromatic heterocyclic ring. When the linked aromatic ring contains at least one heterocycle, it is included in the heteroaryl group.
- a monovalent group generated by removing hydrogen from an aromatic compound in which a plurality of aromatic rings are connected is represented by the following formula, for example.
- Ar 3 to Ar 8 represent a substituted or unsubstituted aromatic ring.
- arylalkyl group and heteroarylalkyl group include groups in which the alkyl group is linked to the aryl group or heteroaryl group.
- aryloxy group, arylalkyloxy group, heteroaryloxy group, and heteroarylalkyloxy group include groups in which an oxy group is linked to the aryl group, arylalkyl group, heteroaryl group, and heteroarylalkyl group. It is done.
- cycloalkyl group examples include a cyclopropyl group, a cyclobutyl group, a cyclopentyl group, a cyclohexyl group, a cycloheptyl group, a cyclooctyl group, and a methylcyclohexyl group, and preferably a cyclopentyl group, a cyclohexyl group, or a methylcyclohexyl group.
- a cyclopropyl group a cyclobutyl group
- a cyclopentyl group a cyclohexyl group
- a cycloheptyl group a cyclooctyl group
- methylcyclohexyl group preferably a cyclopentyl group, a cyclohexyl group, or a methylcyclohexyl group.
- Y 1 and Y 2 represent a single bond or a divalent group, and may be the same or different.
- the divalent group there is a group represented by-(Z 2 ) m- (X) n- (Z 3 ) p- (X) q- , where Z 2 and Z 3 are alkylene and arylene. Or heteroarylene, X is O, COO, S, CONH, CO or the like, and m, n, p, and q are numbers from 0 to 3.
- Z 2 and Z 3 are C 1 to C 20 alkylene groups, C 6 to C 30 arylene groups, C 3 to C 30 heteroarylene groups, and X is CO, COO, or O.
- Y 1 and Y 2 are preferably a single bond, a C 1 to C 6 alkylene group, a C 6 to C 12 arylene group, a C 3 to C 12 heteroarylene group, CO, COO or O. However, Y 1 and Y 2 do not have 5 or more condensed ring structures.
- alkylene group examples include a methylene group, an ethylene group, a propylene group, a butylene group, a pentylene group, a hexylene group, a heptylene group, an octylene group, a nonylene group, and a decylene group, preferably a methylene group, an ethylene group, and a propylene group.
- alkylene groups having 1 to 8 carbon atoms such as a group, butylene group, pentylene group, hexylene group, heptylene group and octylene group.
- the alkylene chain may be linear or branched.
- arylene group and heteroarylene group include groups generated by removing two hydrogens from the aromatic ring exemplified for the R aryl group and heteroaryl group or an aromatic compound in which a plurality of these aromatic rings are connected. .
- W 1 and W 2 represent a polymerizable group, which is a polymerizable group that can be polymerized by light, heat, a catalyst, or the like.
- this polymerizable group include a radical polymerizable group and a cationic polymerizable group.
- the radical polymerizable group is preferably a vinyl group or a substituted vinyl group substituted with an alkyl group having 1 to 6 carbon atoms, more preferably a vinyl group selected from a vinyl group and a substituted vinyl group.
- R 1 , R 2 and R 3 are each a C1-6 hydrogen, alkyl group or phenyl group, preferably hydrogen or a C1-3 alkyl group.
- a cyclic ether group such as an epoxy group or an oxetane group is preferable.
- These cyclic ether groups may have a substituent, and examples of the substituent include an alkyl group having 1 to 6 carbon atoms.
- R 1, Y 1, W 1 is the general formula (1) R, is the same as Y 1, W 1.
- the compound represented by the general formula (2) is further converted into the total number of moles of the compound represented by the general formula (1) and the compound represented by the general formula (2).
- 100 100, it can be contained in an amount of 0 to 95 mol%.
- the compound represented by the general formula (2) is contained in the range of 0 to 70%. .
- Z represents a C 6 -C 30 aryl group, a C 3 -C 30 heteroaryl group or a C 12 -C 60 diarylamino group, preferably a C 6 -C 24 aryl group.
- Y 2 is the same as Y 1 in the general formula (1)
- W 2 is the same as W 1 in the general formula (1).
- the compound represented by the general formula (2) has one polymerizable group.
- the compound represented by the general formula (2) is preferably a charge transporting compound having a polymerizable group, and Z has at least one group represented by the formula (9) inside.
- Ar 1 and Ar 2 independently represent a C 6 -C 30 aryl group, a C 3 -C 30 heteroaryl group, and the aryl group described for R in the general formula (1); Similar to the heteroaryl group, Ar 1 , Ar 2 and N may form a condensed ring. However, Ar 1 and Ar 2 are not 5 or more condensed rings.
- Z in the general formula (2) has at least one group represented by the formula (10) or (11) inside.
- R 2 is the same as R described in the general formula (1).
- the cured composition and cured product of the present invention may be only the compound of the general formula (1), but by introducing the second component, the carrier mobility, the crosslinking density and the like can be adjusted, so that the general formula (2 It is preferable that it is a mixture with the compound shown by this.
- a curable composition may be prepared by mixing a copolymerizable compound, a general organic solvent such as toluene or THF, and various polymerization catalysts such as AIBN, BPO, and phosphotungstic acid.
- a compound having an indolocarbazole skeleton having two polymerizable groups represented by the general formula (1) of the present invention can be easily produced by a known method.
- a compound having two vinyl groups can be produced by the following reaction formula.
- the compound having a polymerizable group represented by the general formula (2) of the present invention can be easily produced by a known method in addition to a commercially available vinyl compound such as diphenylaminostyrene or an acrylic compound such as phenyl acrylate. it can.
- a compound having a vinyl group can be produced by the following reaction formula.
- the cured composition of the present invention may be any compound containing the compound of the general formula (1) alone or a mixture with the compound of the general formula (2).
- Films are formed by a coating method such as a printing method, a printing method, a spray coating method, or a dispenser method, and a cured product obtained by crosslinking or curing with heat, light, a catalyst or the like as it is or after removing a solvent by drying.
- the cured product can be easily cured by a known method.
- a compound represented by the general formula (1) is added to toluene, anisole, THF or the like.
- a dissolved film insoluble in a solvent having a crosslinked structure can be obtained by dissolving in an arbitrary solvent, forming a film by a spin coating method, and then heating the substrate with a hot plate under anaerobic conditions.
- the temperature and curing time can be adjusted under the same conditions as in the case of a single compound, and the polymerizable group can be used as necessary. It can be similarly cured by the addition of the catalyst. Furthermore, in the case of a mixture of two or more types, if the polymerizable group can be copolymerized, the copolymerization proceeds well. In this case, it is advantageous to use the same polymerizable group.
- the curable composition and the cured product of the present invention give an excellent organic electroluminescence device by being contained in the organic layer of the organic EL device.
- at least one organic layer selected from a light emitting layer, a hole transport layer, an electron transport layer, and a hole blocking element layer may be contained. More preferably, it may be contained as a material for the hole transport layer.
- the organic electroluminescent device using the curable composition and the cured product of the present invention has a plurality of organic layers between a pair of an anode and a cathode, particularly a hole transport layer / light-emitting layer / electron transport layer, hole transport. It is preferably composed of a layer / light emitting layer / electron transport layer or a hole transport layer / light emitting layer / electron transport layer. Particularly preferred is a layer structure of hole transport layer / light emitting layer / electron transport layer.
- the organic electroluminescent element of this invention can also provide a protective layer in each after forming each organic layer. Furthermore, a protective film may be provided to protect the entire element from moisture and oxygen.
- the light emitting layer is a layer containing a light emitting material and may be fluorescent or phosphorescent. Alternatively, a light emitting material may be used as a dopant and a host material may be used in combination.
- a light emitting material may be used as a dopant and a host material may be used in combination.
- the fluorescent light emitting material compounds known in various literatures and compounds shown below can be used, but are not limited thereto.
- the phosphorescent material preferably contains an organometallic complex containing at least one metal selected from ruthenium, rhodium, palladium, silver, rhenium, osmium, iridium, platinum and gold.
- organometallic complexes are known in the above-mentioned patent documents and the like, and these can be selected and used.
- Phosphorescent materials for obtaining high luminous efficiency include complexes such as Ir (ppy) 3 having a noble metal element such as Ir as a central metal, complexes such as Ir (bt) 2 ⁇ acac 3 , and PtOEt 3 Complexes are mentioned. Specific examples of phosphorescent light emitting materials are shown below, but are not limited thereto.
- an organic electroluminescent device having various emission wavelengths can be obtained.
- the amount contained in the light emitting layer is preferably in the range of 0.1 to 50% by weight. More preferably, it is 1 to 30% by weight.
- the host material in the light emitting layer a known host material can be used, and the polymer of the present invention can also be used as the host material. Moreover, you may use the polymer of this invention, and another host material together.
- a known host compound that can be used is preferably a compound that has a hole transporting ability and an electron transporting ability, prevents a long wavelength of light emission, and has a high glass transition temperature.
- host materials are known from a large number of patent documents and can be selected from them.
- Specific examples of the host material are not particularly limited, but include indole derivatives, carbazole derivatives, triazole derivatives, oxazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivatives, pyrazolone derivatives, phenylenediamine.
- 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, anthraquino Heterocyclic tetracarboxylic acid anhydrides such as dimethane derivatives, anthrone derivatives, diphenylquinone derivatives, thiopyran dioxide derivatives, naphthalene perylene,
- the curable composition and the cured product of the present invention are advantageously used.
- one or two or more low molecular hole transport compounds such as triphenylamine derivatives and carbazole derivatives of tertiary amines may be used as additives within a range not impairing the object of the present invention. You may mix
- Examples of the electron transport compound that forms the electron transport layer include oxadiazole derivatives, imidazole derivatives, and triazole derivatives. If necessary, one or two or more low molecular electron transport compounds may be blended as additives and used as a composition within a range not impairing the object of the present invention. Specific examples of the electron transporting compound are shown below, but are not limited thereto.
- a hole injection layer may be inserted between the anode and the hole transport layer or the light emitting layer.
- a hole injection material for forming the hole injection layer conductive polymers such as polythiophene derivatives and polypyrrole derivatives can be used. Of these, poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (PEDOT / PSS), which is a polythiophene derivative, is preferable from the viewpoint of hole injection efficiency.
- the thickness is preferably 200 nm or less, more preferably 100 nm or less.
- the soot anode supplies holes to a hole injection layer, a hole transport layer, a light emitting layer or the like, and is generally formed on a glass substrate.
- the anode material used in the present invention is not particularly limited, and specific examples include conductive metal oxides such as indium-tin oxide (ITO) and tin oxide, and metals such as gold, silver, and platinum.
- ITO indium-tin oxide
- tin oxide such as gold, silver, and platinum.
- Commercially available glass with ITO can also be used.
- Commercially available glass with ITO is usually used after cleaning with a cleaning agent aqueous solution and a solvent, and then cleaning with a UV ozone irradiation device or a plasma irradiation device.
- the cathode supplies electrons to the electron transport layer or the light emitting layer
- the anode material used in the present invention is not particularly limited.
- metals such as Li, Mg, Ca, Al and alloys thereof,
- Mg—Ag alloy, Mg—Al alloy and the like can be mentioned.
- the cathode and anode can be formed by a known method, that is, vacuum deposition or sputtering.
- the thickness of the cathode is preferably 300 nm or less, more preferably 200 nm or less, while the thickness of the anode is preferably 200 nm or less, more preferably 100 nm or less.
- a spin coating method is generally used as a method for forming a polymer layer such as a polymer light-emitting material, a polymer material for a hole transport layer, or a polymer material for an electron transport layer.
- a spin coating method is generally used as a method for forming a polymer layer such as a polymer light-emitting material, a polymer material for a hole transport layer, or a polymer material for an electron transport layer.
- examples of the method for forming the organic polymer layer include, but are not limited to, an inkjet method, a printing method, a spray coating method, and a dispenser method.
- Synthesis example 1 Synthesis of Compound (A-3) Compound (A-1) is prepared, and compounds (A-2) and (A-3) are synthesized according to scheme (S-1).
- Tetrahydrofuran was distilled off, ethyl acetate and saturated brine were added, and the mixture was separated into oil and water. The organic layer was dehydrated over anhydrous magnesium sulfate and evaporated under reduced pressure. Purification by silica gel column chromatography twice gave 0.73 g (yield 40%) of white powder compound (A-3).
- Example 2 Solvent-cleaned, UV ozone-treated glass substrate with ITO having a film thickness of 150 nm, poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (PEDOT / PSS) as a hole injection layer: (HCC Stark) Co., Ltd., trade name: Clevios PCH8000) was formed to a film thickness of 25 nm.
- the compound (A-3) was dissolved in tetrahydrofuran to prepare a 0.4 wt% solution, and a film having a thickness of 20 nm was formed as a hole transport layer by a spin coating method.
- the solvent was removed with a hot plate at 150 ° C.
- Alq 3 was formed to a thickness of 35 nm and LiF / Al was formed to a thickness of 170 nm as a cathode, and this element was sealed in a glove box to produce an organic electroluminescent element.
- the organic electroluminescence device When an external power source was connected to the organic electroluminescence device thus obtained and a DC voltage was applied, it was confirmed that the organic electroluminescence device had the light emission characteristics as shown in Table 1.
- the luminance shown in Table 1 is a value at 20 mA / cm 2 .
- the maximum wavelength of the device emission spectrum was 550 nm, and green emission derived from an iridium complex was observed.
- Example 3 Solvent-cleaned, UV ozone-treated glass substrate with ITO having a film thickness of 150 nm, poly (3,4-ethylenedioxythiophene) / polystyrene sulfonic acid (PEDOT / PSS) as a hole injection layer: (HCC Stark) Co., Ltd., trade name: Clevios PCH8000) was formed to a film thickness of 25 nm.
- the compound (A-3) was dissolved in tetrahydrofuran to prepare a 0.4 wt% solution, and a film having a thickness of 20 nm was formed as a hole transport layer by a spin coating method.
- the solvent was removed with a hot plate at 150 ° C.
- thermosetting film is a film having a crosslinked structure and is insoluble in a solvent.
- This thermosetting film is a hole transport layer (HTL).
- HTL hole transport layer
- tris (2- (p-tolyl) pyridine) iridium (III) is used as the light emitting layer dopant, and 4,4′-bis (9H-carbazol-9-yl) biphenyl is used as the light emitting layer host.
- a 1 wt% solution was prepared by dissolving in toluene so as to be 6 wt%, and a 40 nm film was formed as a light emitting layer by spin coating.
- Alq 3 is formed to be 35 nm as an electron transport layer and LiF / Al is formed to a thickness of 170 nm as a cathode, and this element is sealed in a glove box to produce an organic electroluminescent element. did.
- the element evaluation was performed in the same manner as in Example 2.
- the light-emitting layer was formed by spin coating, it was confirmed by using a high-speed spectroscopic ellipsometer (M2000 manufactured by JA Woollam Japan) that the cured film did not dissolve and could be laminated with the light-emitting layer. Yes.
- DPAS diphenylaminostyrene
- Example 5 In Example 3, a device was produced and evaluated in the same manner as in Example 3 except that the following compound (A-4) was used instead of the compound (A-3). Compound (A-4) was synthesized using the method for producing (A-2) from (A-1) shown in Scheme (S-1).
- Example 6 A device was prepared and evaluated in the same manner as in Example 3 except that the following compound (A-5) was used in Example 3. Compound (A-5) was synthesized using the method shown in Scheme (S-1).
- Example 2 a device was produced and evaluated in the same manner as in Example 2 except that the compound (A-3) was not used.
- Example 2 a hole transport layer was prepared using the following compound (B1) instead of (A-3), and UV curing was performed for 90 seconds using an AC power source type UV irradiation device for curing, followed by photopolymerization. A device was prepared and evaluated in the same manner as in Example 2 except that curing was performed.
- Example 3 a device was produced and evaluated in the same manner as in Example 3 except that the compound (A-3) was not used.
- Table 1 shows the compounds used in the positive hole transport layer (HTL), the film formation method of the light emitting layer, and the element evaluation results.
- Example 2 and Comparative Example 1 From Example 2 and Comparative Example 1, it can be seen that an element in which a hole transport layer is formed by a wet process using the compound of the present invention exhibits excellent element characteristics. Further, from Examples 3 to 6 and Comparative Examples 2 and 3, even when the compound of the present invention is used to form a hole transport layer by a wet process and a light emitting layer of an adjacent layer is further formed by a wet process, it is suitable. It can be seen that the film can be laminated and exhibits good light emission characteristics.
- the curable composition and the cured product of the present invention for the organic layer of the organic electroluminescence device, the hole injection property, electron resistance, and charge transport property are improved and the light emission efficiency is excellent.
- an organic layer containing other materials can be laminated on the upper layer by coating, a large-area element can be easily manufactured. Since the organic electroluminescent device using this curable composition or cured product is excellent in luminous efficiency, it can be applied to organic electroluminescent devices used in lighting devices, image display devices, backlights for display devices, etc. Technical value is great.
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Abstract
Description
ここで、ZはC6~C30のアリール基、C3~C30のヘテロアリール基又はC12~C60のジアリールアミノ基をあらわす。Y2は単結合、又は2価の基を表す。W2は重合性基である。なお、Z、R、Y1、Y2は、5環以上の縮合環構造を有しない。
式(3)または(4)中、Y1、W1は一般式(1)と同意であり、R1は一般式(1)のRと同意である。
式(9)中、Ar1、Ar2は、独立にC6~C30のアリール基、C3~C30のヘテロアリール基を表し、Ar1、Ar2とNで縮合環を形成しても構わない。但し、Ar1、Ar2は、5環以上の縮合環構造を有しない。
インドロカルバゾール骨格は、インドール環とカルバゾール環が縮合した5環の縮合環化合物から2つのN位のHを2つとって生じるものである。この骨格は、インドール環とカルバゾール環との縮合可能な位置が複数存在するため、2つのN位の置換基が異なる場合は、下記式(A)~(F)の6種類の構造異性体の基をとり得るが、いずれの構造異性体であってもよい。尚、2つのN位の置換基が同一の場合は、(C)と(F)は同じ構造となり、異性体は5種類となる。インドロカルバゾール骨格は、本発明の効果を阻害しない範囲で、置換基を有することができる。
本発明の硬化性組成物及び硬化物を用いた有機電界発光素子は、一対の陽極と陰極の間に複数の有機層を持ち、特に正孔輸送層/発光層兼電子輸送層、正孔輸送層兼発光層/電子輸送層、または正孔輸送層/発光層/電子輸送層からなることが好ましい。特に好ましくは、正孔輸送層/発光層/電子輸送層の層構造である。また、本発明の有機電界発光素子は、また各有機層を形成した後、それぞれに保護層を設けることもできる。更に、素子全体を水分や酸素から保護するために保護膜を設けてもよい。
発光層における発光材料は、蛍光発光材料としては各種文献で公知の化合物や以下に示すような化合物が使用可能であるが、これに限らない。
化合物(A-3)の合成
化合物(A-1)を用意し、スキーム(S-1)に従い化合物(A-2)及び(A-3)を合成する。
1H-NMR(400MHz、CDCl3 r.t.):δ(ppm);10.149(1H, s)、10.113(1H, s)、8.14-8.21(5H, m)、8.065(1H, dt, J=7, 2)、7.913(1H, dt, J=8, 2)、7.908(1H, dt, J=8, 2)7.846(2H, br t, J=8)、7.21-7.40(6H, m)6.790(1H, ddd, J=2, 7, 8)5.979(1H, d, J=8)
FD-MSスペクトル:464(M+、base)
1H-NMR(400MHz、CDCl3 , r.t.):δ(ppm);8.172(1H, d, J=9),8.150(1H, dd, J=8, 2),7.69-7.72(2H, m),7.58-7.63(3H, m),7.554(1H, dt, J=8, 2),7.524( 1H, ddd, J=9, 2, 1),7.472(1H, dt, J=7, 2),7.30-7.36(3H, m),7.313(1H, d, J=8),7.291(1H, br d, J=8),6.808(1H, dd, J=18, 12),6.804(1H, dd, J=18, 11),6.803(1H, ddd, J=8, 7, 1),6.060(1H, d, J=8),5.832(1H, br d, J=18),5.806(1H, br d, J=18),5.355(1H, d, J=12),5.326(1H, d, J=11)
FD-MSスペクトル:464(M+、base)
溶媒洗浄、UVオゾン処理した膜厚150nmからなるITO付ガラス基板に、正孔注入層としてポリ(3,4-エチレンジオキシチオフェン)/ポリスチレンスルホン酸(PEDOT/PSS):(エイチ・シー・シュタルク株式会社製、商品名:クレビオスPCH8000)を膜厚25nmで製膜した。次に、化合物(A-3)をテトラヒドロフランに溶解して0.4wt%溶液に調製し、スピンコート法により正孔輸送層として20nmを製膜した。次に、嫌気条件下150℃、3時間ホットプレートで溶媒除去し、加熱、硬化を行った。真空蒸着装置を用いて、発光層ドーパントとしてトリス(2-(p-トリル)ピリジン)イリジウム(III)を、発光層ホストとして4,4’-ビス(9H-カルバゾル-9-イル)ビフェニルを用い、ドーパント濃度が0.6wt%となるように共蒸着し、40nm発光層を製膜した。その後、真空蒸着装置を用いて、Alq3を35nm、陰極としてLiF/Alを膜厚170nmで製膜し、この素子をグローブボックス内で封止することにより有機電界発光素子を作製した。
溶媒洗浄、UVオゾン処理した膜厚150nmからなるITO付ガラス基板に、正孔注入層としてポリ(3,4-エチレンジオキシチオフェン)/ポリスチレンスルホン酸(PEDOT/PSS):(エイチ・シー・シュタルク株式会社製、商品名:クレビオスPCH8000)を膜厚25nmで製膜した。次に、化合物(A-3)をテトラヒドロフランに溶解して0.4wt%溶液に調製し、スピンコート法により正孔輸送層として20nmを製膜した。次に、嫌気条件下150℃、1時間ホットプレートで溶媒除去し、加熱、硬化を行った。この熱硬化膜は、架橋構造を有している膜であり、溶剤に不溶である。この熱硬化膜は、正孔輸送層(HTL)である。そして発光層ドーパントとしてトリス(2-(p-トリル)ピリジン)イリジウム(III)を、発光層ホストとして4,4’-ビス(9H-カルバゾル-9-イル)ビフェニルを用い、ドーパント濃度が0.6wt%となるようにトルエンに溶解させ、1wt%溶液調製し、スピンコート法により発光層として40nmを製膜した。その後、真空蒸着装置を用いて、電子輸送層としてAlq3を35nm、陰極としてLiF/Alを膜厚170nmで製膜し、この素子をグローブボックス内で封止することにより有機電界発光素子を作製した。素子評価は、実施例2と同様に行った。尚、発光層をスピンコート製膜した後に、硬化膜が溶解せず、発光層と積層できている事を高速分光エリプソメーター(ジェー・エー・ウーラム・ジャパン社製M2000)を用いて確認している。
実施例3において、化合物(A-3)単独に代えて、化合物(A-3):ジフェニルアミノスチレン(DPAS)=5:5の比率で混合した混合物を使用した以外は、実施例3と同様にして素子を作製、評価した。
実施例3において、化合物(A-3)に代えて,下記化合物(A-4)を使用した以外は、実施例3と同様にして素子を作製、評価した。尚、化合物(A-4)はスキーム(S-1)に示した(A-1)から(A-2)を作る手法を用いて合成した。
実施例3において、下記化合物(A-5)を使用した以外は、実施例3と同様にして素子を作製、評価した。尚、化合物(A-5)はスキーム(S-1)に示した手法を用いて合成した。
実施例2において、化合物(A-3)を使用しなかった以外は、実施例2と同様にして素子を作製、評価した。
実施例2において、(A-3)に代えて下記化合物(B1)を用い正孔輸送層を作成し、硬化に交流電源方式の紫外線照射装置を用いて紫外線を90秒間照射し、光重合して硬化を行った以外は実施例2と同様にして素子を作製、評価した。
実施例3において、化合物(A-3)を使用しなかった以外は、実施例3と同様にして素子を作製、評価した。
Claims (11)
- 一般式(1)で表される化合物と一般式(2)で表される化合物の総モル数を100とした場合、一般式(1)で表される化合物を5~100モル%、一般式(2)で表される化合物を0~95モル%を含有することを特徴とする硬化性組成物。
式(1)中、環Aは隣接環と任意の位置で縮合する式(1a)で表される複素環を表し、Rは水素原子、C1~C20のアルキル基、C1~C20のアルコキシ基、C6~C30のアリール基、C6~C30のアリールオキシ基、C7~C36のアリールアルキル基、C7~C36のアリールアルキルオキシ基、C3~C30のヘテロアリール基、C3~C30のヘテロアリールオキシ基、C4~C36のヘテロアリールアルキル基、C4~C36のヘテロアリールアルキルオキシ基又はC3~C30のシクロアルキル基を表し、同一であっても異なっていてもよい。Y1は単結合、又は2価の基を表し、同一であっても異なっていてもよい。W1は重合性基であり、同一であっても異なっていてもよい。
式(2)中、ZはC6~C30のアリール基、C3~C30のヘテロアリール基又はC12~C60のジアリールアミノ基を表す。Y2は単結合、又は2価の基を表す。W2は重合性基である。 - 一般式(1)、(1a)及び(2)におけるW1、W2が、ラジカル重合性基またはカチオン重合性基であることを特徴とする請求項1に記載の硬化性組成物。
- 一般式(1)、(1a)及び(2)におけるW1、W2が、独立にビニル基、炭素数1~6のアルキル基で置換された置換ビニル基、エポキシ基、オキセタニル基から選ばれる重合性基であることを特徴とする請求項5に記載の硬化性組成物。
- 一般式(1)、(1a)及び(2)におけるW1、W2が、ビニル基及び置換ビニル基から選ばれるビニル基類であり、一般式(1)で表される化合物がビニル基類を2つ有し、一般式(2)で表される化合物がビニル基類を1つ有する請求項1に記載の硬化性組成物。
- 請求項1~7のいずれかに記載の硬化性組成物を硬化させてなる硬化物。
- 一般式(1)で表される化合物が100モル%である硬化性組成物を硬化させてなる請求項8に記載の硬化物。
- 基板上に積層された陽極層及び陰極層の間に有機層を有する有機電界発光素子であって、該有機層の少なくとも一層に請求項8に記載の硬化物を含有することを特徴とする有機電界発光素子。
- 硬化物を含有する有機層が正孔輸送層であることを特徴とする請求項10に記載の有機電界発光素子。
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KR20150070214A (ko) * | 2012-10-18 | 2015-06-24 | 도레이 카부시키가이샤 | 벤즈인돌로카르바졸 유도체, 그것을 사용한 발광 소자 재료 및 발광 소자 |
WO2016006662A1 (ja) * | 2014-07-09 | 2016-01-14 | 日産化学工業株式会社 | 電荷輸送性ワニス、電荷輸送性薄膜及びその製造方法、並びに有機エレクトロルミネッセンス素子及びその製造方法 |
WO2022131346A1 (ja) * | 2020-12-17 | 2022-06-23 | 株式会社Adeka | 化合物及び組成物 |
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EP2725633B1 (en) * | 2011-06-27 | 2018-08-01 | Nippon Steel & Sumikin Chemical Co., Ltd. | Polymer for use in organic electroluminescent element and organic electroluminescent element employing same |
CN108440537B (zh) * | 2018-04-18 | 2021-04-27 | 石家庄诚志永华显示材料有限公司 | 咔唑衍生物、包含该咔唑衍生物的材料和有机电致发光器件 |
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Cited By (8)
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KR20150070214A (ko) * | 2012-10-18 | 2015-06-24 | 도레이 카부시키가이샤 | 벤즈인돌로카르바졸 유도체, 그것을 사용한 발광 소자 재료 및 발광 소자 |
EP2910554A4 (en) * | 2012-10-18 | 2016-06-29 | Toray Industries | BENZINDOLOCARBAZOLE DERIVATIVE MATERIAL MANUFACTURED THEREFOR FOR A LIGHT-EMITTING ELEMENT AND LIGHT-EMITTING ELEMENT |
KR101966680B1 (ko) | 2012-10-18 | 2019-04-09 | 도레이 카부시키가이샤 | 벤즈인돌로카르바졸 유도체, 그것을 사용한 발광 소자 재료 및 발광 소자 |
WO2016006662A1 (ja) * | 2014-07-09 | 2016-01-14 | 日産化学工業株式会社 | 電荷輸送性ワニス、電荷輸送性薄膜及びその製造方法、並びに有機エレクトロルミネッセンス素子及びその製造方法 |
KR20170027790A (ko) | 2014-07-09 | 2017-03-10 | 닛산 가가쿠 고교 가부시키 가이샤 | 전하 수송성 바니시, 전하 수송성 박막 및 그 제조 방법, 그리고 유기 일렉트로 루미네선스 소자 및 그 제조 방법 |
JPWO2016006662A1 (ja) * | 2014-07-09 | 2017-04-27 | 日産化学工業株式会社 | 電荷輸送性ワニス、電荷輸送性薄膜及びその製造方法、並びに有機エレクトロルミネッセンス素子及びその製造方法 |
US10211412B2 (en) | 2014-07-09 | 2019-02-19 | Nissan Chemical Industries, Ltd. | Charge-transporting varnish, charge-transporting thin film and method for manufacturing same, and organic electroluminescent element and method for manufacturing same |
WO2022131346A1 (ja) * | 2020-12-17 | 2022-06-23 | 株式会社Adeka | 化合物及び組成物 |
Also Published As
Publication number | Publication date |
---|---|
US20140008626A1 (en) | 2014-01-09 |
EP2692747B1 (en) | 2018-09-19 |
JPWO2012132501A1 (ja) | 2014-07-24 |
KR20140034165A (ko) | 2014-03-19 |
EP2692747A1 (en) | 2014-02-05 |
US9590179B2 (en) | 2017-03-07 |
TWI507407B (zh) | 2015-11-11 |
CN103443140B (zh) | 2015-07-08 |
EP2692747A4 (en) | 2014-10-01 |
TW201245196A (en) | 2012-11-16 |
KR101775933B1 (ko) | 2017-09-07 |
JP5770833B2 (ja) | 2015-08-26 |
CN103443140A (zh) | 2013-12-11 |
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