US20020001734A1 - Organic luminous material and organic light-emitting device - Google Patents
Organic luminous material and organic light-emitting device Download PDFInfo
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- US20020001734A1 US20020001734A1 US09/842,228 US84222801A US2002001734A1 US 20020001734 A1 US20020001734 A1 US 20020001734A1 US 84222801 A US84222801 A US 84222801A US 2002001734 A1 US2002001734 A1 US 2002001734A1
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- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
- C08F38/00—Homopolymers and copolymers of compounds having one or more carbon-to-carbon triple bonds
-
- C—CHEMISTRY; METALLURGY
- C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
- C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
- C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
- C08G61/02—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
- C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
- H10K85/10—Organic polymers or oligomers
- H10K85/151—Copolymers
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/10—Non-macromolecular compounds
- C09K2211/1018—Heterocyclic compounds
- C09K2211/1025—Heterocyclic compounds characterised by ligands
- C09K2211/1092—Heterocyclic compounds characterised by ligands containing sulfur as the only heteroatom
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- C—CHEMISTRY; METALLURGY
- C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
- C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
- C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
- C09K2211/14—Macromolecular compounds
- C09K2211/1408—Carbocyclic compounds
- C09K2211/1425—Non-condensed systems
-
- H—ELECTRICITY
- H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
- H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
- H10K50/00—Organic light-emitting devices
- H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
- H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
-
- Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10—TECHNICAL SUBJECTS COVERED BY FORMER USPC
- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to an organic luminous material and an organic light-emitting device and, more particularly, an organic luminous material and an organic light-emitting device like an organic electroluminescence (EL) device employing such material.
- EL organic electroluminescence
- the display device employing the organic EL device can provide the high brightness and full color display by the low voltage driving.
- the display device consisting of the organic EL devices has features different from the liquid crystal display (LCD).
- LCD liquid crystal display
- the light weight and low cost product that has no viewing angle dependence because it is the spontaneously emissive display, does not need the back lights because of the high contrast, has a quick response speed, has the easy film formation characteristic, and stands the impact since the overall device is constructed by the solid state elements.
- the organic EL device has a structure in which the lower electrode formed of transparent conductive material, the organic thin film (luminous layer), and the upper electrode formed of magnesium, potassium, etc. are formed in sequence on the glass substrate, for example, and a thickness of the overall structure can be reduced up to about several mm. Then, the light is emitted from the luminous layer by applying the DC voltage between the lower electrode and the upper electrode, and this light is passed through the lower electrode and the glass substrate to output to the outside.
- the organic EL device is the injection electroluminescence device that increases the number of carriers in operation by injecting the carriers from the electrode to thus emit the light by the recombination. Sometimes the organic EL device is also called the organic LED.
- the luminous material employed in the organic thin film of the organic EL device there are the monomer material and the polymer material. Normally the film of the monomer material is formed by the vacuum evaporation method, and normally the film of the polymer material is formed by the coating method. The coating method is practical in device formation because the expensive equipment is not needed.
- PPV poly p-phenylenevinylena
- the EL device employing such material is set forth in Patent Application Publication (KOKAI) Hei 10-326675, for example.
- the conjugated polymer material such as PPV employed as the luminous layer in the prior art is in the high crystallinity state at the normal temperature, unlike the normal polymer material.
- the luminous layer polymer in the prior art which is ready to crystallize, is insoluble in the organic solvent, any treatment must be applied, e.g., the polymer must be mixed into the organic solvent while heating, when the polymer is coated on the substrate, and thus it is not easy to handle the polymer.
- the conjugated polymer in the prior art is solved in the organic solvent, such polymer is still ready to crystallize after the cooling.
- an organic light-emitting device which comprises a lower electrode; a luminous layer formed on the lower electrode and made of polymer indicated by
- Ar 1 denotes a first allylene group
- Ar 2 denotes a second allylene group
- R 1 denotes a first substituent
- R 2 denotes a second substituent
- R 3 denotes a third substituent
- R 4 denotes a fourth substituent
- n denotes a copolymerization ratio
- the polymer employed as the luminous layer of the organic light-emitting device and given by the chemical formula (1) has low crystallinity at the normal temperature and the room temperature and has good solubility rater than the polymer for the luminous layer in the prior art.
- the polymer given by the chemical formula (1) is left as the flat film after such polymer is dissolved in the solvent, then this polymer is coated on the substrate, and then the solvent is removed.
- the organic light-emitting device is constructed by putting the polymer given by the chemical formula (1) between the upper electrode and the lower electrode, the local electric field concentration is hard to occur, the short-circuit between the upper electrode and the lower electrode is hard to occur, and the yield of the device can be improved.
- first allylene group of the polymer is a paraphenylene group and the second allylene group is a metaphenylene group, and the polymer is given by
- the chemical formula (2) shows the material that can emit the light in the green color wavelength band and its near emission wavelength band.
- the material that can emit the light in the red color wavelength band and its near emission wavelength band or the material that can emit the light in the blue color wavelength band and its near emission wavelength band is needed.
- Ar 2 denotes an allylene groups
- R 1 denotes a first substituent
- R 2 denotes a second substituent
- R 3 denotes a third substituent
- R 4 denotes a fourth substituent
- m and k denote copolymerization ratio
- n denotes a polymerization ratio.
- the aromatic ring constituting the allylene group consists of any one of thiophene, anthracene, pyridine, phenol, aniline, and each derivative of them.
- first substituent, the second substituent and the third substituent consist of any one of hydrogen atom, alkyl group, alkoxy group, carboxyl group, cyano group, phenyl group, biphenyl group, and cyclohexylphenyl group respectively.
- Ar denotes an allylene group
- R 1 denotes a first substituent
- R 2 denotes a second substituent
- n denotes a polymerization ratio.
- the aromatic ring constituting the allylene group consists of any one of thiophene, anthracene, pyridine, phenol, aniline, and each derivative of them.
- the substituent consists of any one of hydrogen atom, alkyl group, alkoxy group, carboxyl group. cyano group, phenyl group, biphenyl group, and cyclohexylphenyl group.
- Ar denotes an allylene group
- R 1 denotes a first substituent
- R 2 denotes a second substituent
- R 3 denotes a third substituent
- R 4 denotes a fourth substituent
- R 5 denotes a fifth substituent
- R 6 denotes a sixth substituent
- m and k denotes copolymerization ratio
- n denotes polymerization ratio.
- the aromatic ring constituting the allylene group consists of any one of benzene, pyrrole, thiophene, carbazole, furan, fluorine, naphthalene, anthracene, and each derivative of them.
- first, second, third, fourth, fifth, and sixth substituents consist of any one of hydrogen atom, alkyl group, alkoxy group, carboxyl group, cyano group, phenyl group, biphenyl group, and cyclohexylphenyl group respectively.
- Ar 3 denotes a first allylene group
- Ar 4 denotes a second allylene group
- R 11 denotes a first substituent
- R 12 denotes a second substituent
- R 13 denotes a third substituent
- R 14 denotes a fourth substituent
- x,y,z denote a copolymerization ratio respectively
- n denotes a polymerization ratio.
- the aromatic ring constituting the first allylene group and the second allylene group consists of any one of benzene, pyrrole, thiophene, carbazole, furan, fluorine, naphthalene, anthracene, and each derivative of them.
- first substituent, the second substituent, the third substituent, and the fourth substituent consist of any one of hydrogen atom, alkyl group, alkoxy group, carboxyl group, cyano group, phenyl group, biphenyl group, and cyclohexylphenyl group respectively,
- FIGS. 1A to 1 D are sectional views showing steps of manufacturing an organic EL device according to an embodiment of the present invention.
- FIG. 2 is a graph showing a change of fluorescent spectrum of a luminous layer employed in the organic EL device in manufacturing process according to the first embodiment of the present invention
- FIG. 3 is a graph showing an EL spectrum with respect to the luminous wavelength emitted by the luminous layer employed in the organic EL device according to the first embodiment of the present invention.
- FIG. 4 is a graph showing a fluorescent spectrum of a red color luminous layer employed in the organic EL device according to the first embodiment of the present invention
- FIG. 5 is a graph showing a fluorescent spectrum of a red color luminous layer employed in the organic EL device according to the second embodiment of the present invention.
- FIG. 6 is a graph showing a fluorescent spectrum of a blue color luminous layer employed in the organic EL device according to the third embodiment of the present invention.
- FIG. 7 is a graph showing a fluorescent spectrum of a blue color luminous layer employed in the organic EL device according to the fourth embodiment of the present invention.
- FIGS. 1A to 1 D are sectional views showing steps of manufacturing an organic EL device according to an embodiment of the present invention.
- an ITO (indium tin oxide) film of 200 nm thickness is formed on a glass (transparent) substrate 1 as a lower electrode (anode) 2 by the sputter method.
- the ITO film is exposed to the oxygen, the ozone plasma, or the like to clean the surface.
- the constituent material of the lower electrode 2 is not limited to ITO, transparent conductive materials such as IDIXO (indium zinc oxide) and others may be employed.
- the polymer given by a following chemical formula (7) is formed as a luminous layer 3 on the lower electrode 2 by the spin coating method to have a thickness of 150 nm, for example.
- n 0.5.
- a solution is prepared by solving the polymer into the solvent, e.g., chloroform (CHCl 3 ) at the normal temperature. Then, as shown in FIG. 1B the solution 3 a is coated on the lower electrode 2 , and then the solvent is removed by the drying.
- the drying temperature is set to more than the vaporization temperature of the solvent but less than 150° C. If the solvent is dried at 150° C., the drying time is set to about 30 minutes.
- the preferable drying conditions are the drying temperature of 90° C. and the drying time of 60 minutes.
- the polymer left on the lower electrode 2 and given by the chemical formula (7) is employed as the luminous layer 3 .
- a magnesium silver (MgAg) of 300 nm thickness is formed as an upper electrode (cathode) on the luminous layer 3 by the co-evaporation method.
- This co-evaporation method used to form the magnesium silver is such a method that evaporation sources are arranged separately every constituent element in the evaporation chamber and then they are evaporated toward the same substrate to form the alloy.
- the upper electrode 4 is formed of the MgAg film in which the magnesiumn and the sliver are alloyed at the rate of 1:10.
- the upper electrode 4 may be grown by the evaporation while patterning the upper electrode 4 by placing a metal mask between the evaporation sources and the substrate.
- metals containing the alkaline metal or the alkaline earth metal such as Na, NaK, Mg, Li, CaMg/Cu mixture, Mg/In alloy, etc. may be employed.
- the green light is emitted from the light-emitting device.
- the light is passed through the lower electrode and the glass substrate 1 and then emitted to the outside.
- the polymer given by the chemical formula (7) since the polymer given by the chemical formula (7) has low crystallinity at the normal temperature and the room temperature and has good solubility in the solvent, the surface of the polymer left after the drying is flat rather than the prior art. Thus, the short-circuit between the upper electrode and the lower electrode can be prevented and yield of the device can be improved.
- the fluorescent spectrum in the state the polymer given by the chemical formula (7) is dissolved into the chloroform is a profile indicated by a broken line in FIG. 2, and the fluorescent spectrum of the polymer in the film state after the chloroform is removed is a profile indicated by a solid line in FIG. 2.
- the polymer in the film state can emit the light in the range of 500 to 550 nm.
- the copper (I) chloride of 150 mg (1.5 mmol) and N,N,N′,N′-tetramethylethylenediamine (TMEDA) of 180 mg (1.5 mmol) are added into the tetrahydrofuran (THF) solution of 180 mil liter (mL).
- THF tetrahydrofuran
- the catalyst is formed by supplying the oxygen into these mixtures for 10 minutes.
- the THF reactive solution obtained by the oxidative condensation polymerization reaction is concentrated up to about 10 mL, and then the concentrate is dropped into the 1-liter 2N-HCL/MeOH solution that is hardly stirred. Then, the polymer generated by the oxidative condensation polymerization reaction is precipitated in the 2N-HCL/MeOH solution, then the catalyst is removed, and then the polymer is purified.
- the precipitated polymer is filtrated/recovered by using the glass filter, and then a small amount of polymer is dissolved once again in the THF solution of 10 mL, for example. and then the polymer is reprecipitated by dropping such polymer into a large amount, e.g., 1 liter, of MeOH liquid.
- the MeOH liquid is used in the situation that it is strongly stirred.
- the product is refined by filtrating/recovering the reprecipitated polymer once again by using the glass filter. Then, the polymer is dried by the vacuum drying. The yield was 95%,
- the polymer indicated by ⁇ circle over (3) ⁇ in the reaction formula (10) is the structure representing the progress of synthesis, and is the same substance as the polymer in the chemical formula (7).
- the polymer given by the chemical formula (7) is employed as the lumninous layer 3 of the organic EL device, but the general formula of the polymer can be given by a following chemical formula (11).
- Ar 1 , Ar 2 denote an allylene group (aromatic ring of two valence) respectively.
- aromatic ring constituting the allylene group there are benzene, pyrrole, thiophene, carbazole, furan, fluorine, naphthalene, anthracene, and each derivative of them.
- the first unit which includes Ar 1 have two of triple bond of carbons
- the second unit which includes Ar 2 have two of triple bond of carbons.
- allylene group for example, there are biphenyl, terphenyl, perylene, coumalin, diphenylamine, triphenylamine, phenanthrene, phenanthridine, phenanthroline, phenylazobenzene, diphenylazobeazene, anthraquinone, acridinone, quinacridone, stilbenzene, and each derivative of them.
- Ar 1 there is the allylene group such as 1,4-phenylene(para(p-)phenylene) group, 1,5 naphthalene group, ect., which has a structure to enhance the rigidity of the polymer.
- Ar 3 there is the allylene group such as 1,3-phenylene(meta(m-)phenylene) group, 1,2 naphthalene group, ect., which has a struture to reduce the rigidity of the polymer.
- R 1 , R 2 , R 3 , R 4 are a substituent such as hydrogen atom, alkyl group, alkoxy group, carboxyl group, cyano group, phenyl group, biphenyl group, cyclohexylphenyl group, and others respectively. Also, all R 1 , R 2 , R 3 , R 4 are different kind, or some of them are same kind, or all of them are same kind.
- n in the chemical formula (11) is a copolymerization ratio and preferably n is set to 0 ⁇ n ⁇ 0.9.
- the polymer having n-1 for example, there is polyallylene butadienylene. In this case, it was confirmed that the crystallinity at the normal temperature is lowered rather than the prior art and the solubility is increased rather than the prior art.
- the luminous wavelength at the luminous layer 3 is changed by selecting above R 1 , R 2 , R 3 , R 4 , Ar 1 , Ar 2 appropriately. Accordingly, if the color image is needed. the pattern in which the structure of the polymer is changed every pixel of the image is formed.
- the first unit is defined as A and the second unit is defined as B.
- A, B have the structure given by the chemical formula (7) respectively, i.e., if the unit A has the structure of the para-substitution product and the unit B has the structure of the meta-substitution product
- n the copolymerization ratio
- the structure that outputs the light from the glass substrate side is employed.
- the light may be output from the upper side by reversing the structure of the electrodes and forming the light transparent conductive film on the upper side.
- the structure in which the luminous layer is directly put between a pair of electrodes is shown. In this case, an organic electron transmitting layer may be formed between the luminous layer and the negative side electrode, otherwise an organic hole transmitting layer may be formed between the luminous layer and the positive side electrode.
- the polymer given by the chemical formula (7) can emit the light in the emitting wavelength range of 500 to 550 nm, i.e., at the green color wavelength and its near emission wavelength.
- the copolymerized polymer used as the red color luminous layer 3 is given by the chemical formula (12).
- an aromatic ring Ar 1 in the chemical formula (11) denotes a benzene ring
- a substituent R 4 denotes the hydrogen atom
- Ar 2 denotes an allylene group
- the aromatic ring is any one of thiophene, anthracene, pyridine, phenol, aniline, and each derivative of them.
- R 1 , R 2 , R 3 and R 4 denote the substituent respectively, and are any one of hydrogen atom, alkyl group, alkoxy group, carboxyl group, cyano group, phenyl group, biphenyl group, and cyclohexylphenyl group respectively.
- m and k denote copolymerization ratio.
- n denotes a polymerization ratio.
- the luminous layer 3 formed of the copolymerized polymer given by the chemical formula (13) has the spectrum shown in FIG. 4, and the peak in the luminous wavelength band is 574 nMn.
- the polymer given by the chemical formula (13) can be synthesized in the same manner as mentioned above by using 3-dodecyloxycarbonyl-2,5-bis(trimethylsilylethynyl)thiophen instead of 4-dodecyloxy-1,3-diethynylbenzene shown in the chemical formula (9).
- homopolymer may be employed in place of the above copolymerized polymer.
- the homopolymer there is poly(3-dodecyloxycarbonyl-2,5-thienylenebutadiynylene) given by the chemical formula (14), for example.
- the spectrum of the hornopolymer given by the chemical formula (13) is shown in FIG. 5, and has the peak at 596 nm in the luminous wavelength band.
- the homopolymer given by the chemical formula (14) can be synthesized as follows.
- the reaction solution in which the reaction given by the chemical formula (15) by stirring them for a night is injected into a mixed solution of the saturated sodium sulfate liquid of 100 mL and the water of 600 mL, and then the resultant deposit is recovered.
- the white needle-like crystal of 9.38 g can be obtained at the yield of 82.0% by recrystallizing the deposit in the ethanol/water mixed solution.
- the white needle-like crystal is the crystal of 2,5-dibromo-3-thenoic acid shown on the right side of the reaction formula (15).
- the white crystal of 8.56 g (18.8 mmol) is obtained at the yield 94.2% by filtering the reaction salt, and then purifying the dichloromethane by using the silica gel column employed as the developing solvent.
- the white crystal is the crystal of 2,5-dibromo-3-dodecyloxycarbonnylthiophene, i.e. dodecyl2,5-dibromo-3-thenoate, shown on the right side of the chemical formula (16).
- 3-dodecylester-2,5-dibromothiophene of 6.81 g (15 mmol), copper iodide (CuI) of 103 mg (0.54 mmol), triphenylphosphine (PPh 3 ) of 210 mg (0.8 mmol) are added into the mixed solution of triethylamine (Et 3 N) of 27 mL and pyridine of 18 mL in the argon atmosphere. Then, this solution is stirred for twenty minutes while applying the argon-bubbling.
- the yellow oil is 3-ddecyloxycarbonyl-2,5-bis(trimethylsilylethynyl)thiophene, i.e., dodecyl-2,5-bis(trimethlsilylethynyl)-3-thenoate, that is obtained by the reaction given by the reaction formula (17).
- the yellow oil of 0.500 g (1 mmol) is dissolved into THF of 20 ML and then 1M tetrabutylammonium fluoride (Bu 4 NF) of 0.5 mL (0.5 mmol) in another THF is added. Then, this solution is stirred for five minutes, and then the purified product is obtained by purifying THF by virtue of the silica gal column used as the developing solvent.
- Bu 4 NF tetrabutylammonium fluoride
- the catalyst solution is formed by adding copper (I) chloride of 10 mg (0.1 mmol), N,N,N′, N′-tetramethylethylenediamine (TMEDA) of 12 mg (0.1 mmol), THF of 8 mL, and pyridine of 2 mL into another vessel, and then supplying oxygen into the liquid in this vessel. Then, THF of 10 mL containing the above purified product is added in the catalyst solution, and then the reaction given by the reaction formula (18) is generated by stirring this for two days in the oxygen atmosphere.
- the general formula of the homopolymer, that can emit the light in the red color wavelength band and its near emission wavelength band, according to the present embodiment is given by the chemical formula (19).
- the aromatic ring constituting Ar is any one of thiophene, anthracene, pyridine, phenol, aniline, and each derivative of them.
- R 1 denotes a first substituent
- R 2 denotes a second substituent.
- the first substituent and second substituent consist of any one of hydrogen atom, alkyl group, alkoxyl group, carboxyl group, cyano group, phenyl group, biphenyl group, and cyclohexylphenyl group respectively.
- n denotes a polysine
- the polymer that can emit the light in the green color wavelength band and its near emission wavelength band or in the red color wavelength band and its near emission wavelength band is explained.
- the polymer that can emit the blue color light is further required. Therefore, the polymer that can emit the light in the blue color wavelength band will be explained hereunder.
- copolymerized polymer constituting the blue color luminous layer 3 for example, there is copoly(4,4′-biphenylylenebutadiynylene) (4-dodecyloxy-m-phenylenebutadiynylene) as given by the chemical formula (20)
- the spectrum of the polymer given by the chemical formula (20) is shown in FIG. 6 and has peaks at 428 nm and 450 nm in the luminous wavelength band.
- the reaction in the chemical formula (21) is caused by adding 4,4′-dibromobiphenyl of 6.24 g (20 mmol), palladium chloride of 354 mg (2 mmol), copper acetate (Cu(CH 3 COO) 2 ) of 364 mg (2 mmol), triphenylphosphine of 1.73 g (6.6 mmol), and trimethylsilylacetylene of 3.24 g (3.3 mmol) into the liquid, that contains triethylamine of 100 mL and THF of 130 mL, in the argon atmosphere, and then refluxing this liquid at 85° C. for a night.
- the white plate-like crystal of 5.90 g (17 mmol) is obtained at the yield of 85.0% by extracting the liquid by the dichloromethane and the water, then processing the resultant oil layer by the silica gel column chromatography using the dichloromethane developing solvent, and then purifying the oil based on the recrystallization using the methanol.
- This white plate-like crystal is 4′-bis(trimethylsilylethynyl)biphenyl shown on the right side of the chemical formula (21).
- the white plate-like crystal of 5.9 g (17 mmol) is dissolved into the THF of 10 mL, then sodium methoxide (NaOCH 3 ) of 1.83 g (34 mmol) that is dissolved in the methanol (CH 3 OH:MeOH) of 6 mL is added into this solution, and then they are reacted at a room temperature for three hours. Then, the oil layer is obtained by the extraction using dichloromethane and 10% hydrochloric acid aqueous solution.
- the oil layer is purified by the silica gel column employing the developing solvent that contains dichloromethane and hexane at a rate of 1:1, whereby the white powder of 1.20 g (5.9 mmol) is obtained at the yield of 34.8%.
- This white powder is 4,4′-diethylbiphenyl shown on the right side of the chemical formula (22).
- copoly((4,4′-biphenylenebutadiynylene) (4-dodecyloxy-m-phenylenebutadiynylene)) is synthesized based on the reaction given by the reaction formula (23) using the white powder.
- the catalyst solution is formed by putting copper (I) chloride of 20 mg (0.2 mmol), TMEDA of 24 mg (0.2 mmol), and THF of 40 mL into the vessel to react with each other, and then supplying oxygen into this reaction solution. Then, 4,4′-diethylbiphenyl of 24 mg and 4-dodecyloxy-m-diethynylbenzene of 311 mg (1 mmol), that are dissolved in THF of 40 mL, are added to the catalyst solution respectively, and then they are stirred in the oxygen atmosphere for two days. This 4-dodecyloxy-m-diethynylbenzene is expressed by the second chemical structural formula from the left in the chemical formula (23).
- the reaction given by the chemical formula (23) makes progress in the middle of this stirring, then the resultant reaction solution is dropped into 2-normal methanol hydrochloride of 500 mL, and then the resultant precipitate is recovered. Then, this precipitate is dissolved into the chloroform to remove the insoluble component, then this solution is dropped into methanol of 500 mL, and then the resultant precipitate is recovered, whereby the white powder of 248 g (0.98 mmol) is obtained at the yield of 48.7%.
- This white powder is the polymer given by the chemical formula (20).
- the luminous layer 3 can emit the blue light or the light close to the blue.
- Ar denotes an allylene group that is any one of benzene, pyrrole, thiophene, carbazole, furan, fluorine. naphthalene, anthracene or each derivative of then.
- R 1 is the first substituent
- R 2 is the second substituent
- R 3 is the third substituent
- R4 is the fourth substituent
- R 5 is the fifth substituent
- R 6 is the sixth substituent which consists of any one of hydrogen atom, alkyl group, alkoxyl group, carboxyl group, cyano group, phenyl group, biphenyl group, and cyclohexylphenyl group respectively.
- m and k denote co-polymerization ratio
- n denotes a polymerization ratio.
- the copolymerized polymer constituting the blue color luminous layer there is the structure given by the chemical formula (25), for example.
- the spectrum of the polymer given by the chemical formula (25) is shown in FIG. 7 and has peaks at 405 nm, 495 nm, and 512 nm in the luminous wavelength band.
- x: y:z is 6:3:1
- the catalyst solution is formed by supplying oxygen into the reaction solution in which copper (I) and THF of 20 mL are mixed. Then, 2,5-didodecyloxy-p-diethynylbenzene of 297 mg (0.6 mmol), 4-dodecyloxy-m-diethynylbenzene of 93 mg (0.3 mmol), and 1,3,5-triethynylbenzene of 15 mg (0.1 mmol) are added into THF of 20 mL, then this solution is added to the above catalyst solution, and then the resultant solution is stirred in the oxygen atmosphere for two days. Accordingly, the reaction given by the reaction formula (26) is generated.
- reaction solution is dropped into 2-normal methanol hydrochloride of 500 mL, and then the resultant precipitate is recovered. Then, this precipitate is dissolved into the chloroform, then this solution from which the insoluble component is removed is dropped into methanol of 500 mL, and then the resultant precipitate is recovered, whereby the yellow powder of 304 g is obtained at the yield of 75.4%.
- the general formula of the copolymerized polymer according to the present embodiment, that emits the light in the blue color wavelength band and its near emission wavelength band, is expressed by the chemical formula (27).
- Ar 3 and Ar 4 denote an allylene group (dihydric aromatic ring) respectively.
- the aromatic ring constituting the allylene group there are benzene, pyrrole, thiophene, carbazole, furan, fluorine, naphthalene, anthracene or each derivative of them.
- allylene group for example, there are biphenyl, terphenyl, perylene, coumalin, diphenylamine, triphenylanine, phenanthrene, phnanthridine, phenanthroline, phenylazobenzene, anthraquinone, acridinone, quinacridone, stilbenzene and each derivative of them.
- R 11 , R 12 , R 13 , R 14 are the substituent respectively, which consists of any one of hydrogen atom, alkyl group, alkoxy group, carboxyl group, cyano group, phenyl group, biphenyl group, cyclohexylphenyl group, and others.
- R 11 , R 12 , R 13 , R 14 are all different types, or some of them are the same types, or R 11 , R 12 , R 13 , R 14 are all same types.
- x, y, z denote copolymerization ratio
- n denotes a polymerization ratio.
- the luminous layer made of the polymer shown in the above chemical formula (11), (12), (19), (24), and (27) are formed between the lower electrode and the upper electrode respectively.
- such polymer is hard to crystallize at the normal temperature and has the high solubility tn the solvent.
- the planarization of the luminous layer can be facilitated, the short-circuit between the upper electrode and the lower electrode hardly occurs, and the yield of the device can be improved.
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JP2001-125359 | 2001-04-24 | ||
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EP (5) | EP1760799B1 (fr) |
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Cited By (7)
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US20060199928A1 (en) * | 2005-03-07 | 2006-09-07 | Tang Ben Z | Hyber-branched diacetylene polymers and their use in ceramics, photonic devices and coating films |
US9112154B2 (en) | 2009-01-20 | 2015-08-18 | Sumitomo Chemical Company, Limited | Metaphenylene polymer compound and light emitting device using the same |
US11003008B2 (en) | 2016-08-04 | 2021-05-11 | Nitto Denko Corporation | Heterocyclic liquid crystal composition, reverse-mode polymer dispersed liquid crystal element, and associated selectively dimmable device |
US11001757B2 (en) | 2017-08-04 | 2021-05-11 | Nitto Denko Corporation | Heterocyclic liquid crystal composition, reverse-mode polymer dispersed liquid crystal element, and selectively dimmable device |
US11186773B2 (en) | 2016-04-13 | 2021-11-30 | Nitto Denko Corporation | Liquid crystal compositions, mixtures, elements, and dimmable devices |
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JP2011099114A (ja) * | 2000-04-27 | 2011-05-19 | Fujitsu Ltd | 有機発光材料 |
JP4341529B2 (ja) * | 2004-11-05 | 2009-10-07 | セイコーエプソン株式会社 | 電子デバイス、電子デバイスの製造方法および電子機器 |
KR100721562B1 (ko) * | 2004-12-03 | 2007-05-23 | 삼성에스디아이 주식회사 | 마그네슘-칼슘 막인 캐소드를 구비하는 유기전계발광소자및 그의 제조방법 |
JP5212677B2 (ja) * | 2006-03-10 | 2013-06-19 | 株式会社リコー | π共役ポリマー |
US20140071392A1 (en) * | 2012-09-07 | 2014-03-13 | Apple Inc. | Initial contact control for lamination |
US10005956B2 (en) * | 2014-11-26 | 2018-06-26 | Massachusetts Institute Of Technology | Compositions, articles, and methods for down-converting light and other applications |
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US20060199928A1 (en) * | 2005-03-07 | 2006-09-07 | Tang Ben Z | Hyber-branched diacetylene polymers and their use in ceramics, photonic devices and coating films |
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US11186773B2 (en) | 2016-04-13 | 2021-11-30 | Nitto Denko Corporation | Liquid crystal compositions, mixtures, elements, and dimmable devices |
US11003008B2 (en) | 2016-08-04 | 2021-05-11 | Nitto Denko Corporation | Heterocyclic liquid crystal composition, reverse-mode polymer dispersed liquid crystal element, and associated selectively dimmable device |
US11001757B2 (en) | 2017-08-04 | 2021-05-11 | Nitto Denko Corporation | Heterocyclic liquid crystal composition, reverse-mode polymer dispersed liquid crystal element, and selectively dimmable device |
US11806577B1 (en) | 2023-02-17 | 2023-11-07 | Mad Dogg Athletics, Inc. | Programmed exercise bicycle with computer aided guidance |
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EP1158839B1 (fr) | 2009-06-17 |
EP1768466B1 (fr) | 2010-01-20 |
KR100816711B1 (ko) | 2008-03-27 |
DE60137375D1 (de) | 2009-02-26 |
EP1760799A2 (fr) | 2007-03-07 |
EP1741765A3 (fr) | 2007-06-27 |
KR20070015492A (ko) | 2007-02-05 |
EP1768466A2 (fr) | 2007-03-28 |
US6846580B2 (en) | 2005-01-25 |
EP1768466A3 (fr) | 2007-06-27 |
DE60141184D1 (de) | 2010-03-11 |
DE60138982D1 (de) | 2009-07-30 |
EP1760799A3 (fr) | 2007-06-27 |
JP4763912B2 (ja) | 2011-08-31 |
KR100914442B1 (ko) | 2009-08-28 |
KR20010098854A (ko) | 2001-11-08 |
KR100816712B1 (ko) | 2008-03-27 |
KR20070015491A (ko) | 2007-02-05 |
EP1768465B1 (fr) | 2009-12-16 |
EP1768465A2 (fr) | 2007-03-28 |
US20040155577A1 (en) | 2004-08-12 |
KR100791527B1 (ko) | 2008-01-04 |
EP1741765A2 (fr) | 2007-01-10 |
DE60142369D1 (de) | 2010-07-22 |
EP1760799B1 (fr) | 2010-06-09 |
EP1158839A3 (fr) | 2006-01-11 |
EP1158839A2 (fr) | 2001-11-28 |
DE60140826D1 (de) | 2010-01-28 |
KR20070015490A (ko) | 2007-02-05 |
EP1741765B1 (fr) | 2009-01-07 |
JP2002170683A (ja) | 2002-06-14 |
EP1768465A3 (fr) | 2007-06-27 |
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