WO2006001198A1 - Composé organique fluorescent blanc - Google Patents

Composé organique fluorescent blanc Download PDF

Info

Publication number
WO2006001198A1
WO2006001198A1 PCT/JP2005/010910 JP2005010910W WO2006001198A1 WO 2006001198 A1 WO2006001198 A1 WO 2006001198A1 JP 2005010910 W JP2005010910 W JP 2005010910W WO 2006001198 A1 WO2006001198 A1 WO 2006001198A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
fluorescent compound
organic fluorescent
white organic
alkyl group
Prior art date
Application number
PCT/JP2005/010910
Other languages
English (en)
Japanese (ja)
Inventor
Tadao Nakaya
Atsushi Ikeda
Mitukura Sato
Original Assignee
Hirose Engineering Co., Ltd.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Hirose Engineering Co., Ltd. filed Critical Hirose Engineering Co., Ltd.
Publication of WO2006001198A1 publication Critical patent/WO2006001198A1/fr

Links

Classifications

    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/88—Carbazoles; Hydrogenated carbazoles with hetero atoms or with carbon atoms having three bonds to hetero atoms with at the most one bond to halogen, e.g. ester or nitrile radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D403/00—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00
    • C07D403/02—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings
    • C07D403/12—Heterocyclic compounds containing two or more hetero rings, having nitrogen atoms as the only ring hetero atoms, not provided for by group C07D401/00 containing two hetero rings linked by a chain containing hetero atoms as chain links
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D471/00—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00
    • C07D471/22—Heterocyclic compounds containing nitrogen atoms as the only ring hetero atoms in the condensed system, at least one ring being a six-membered ring with one nitrogen atom, not provided for by groups C07D451/00 - C07D463/00 in which the condensed systems contains four or more hetero rings
    • 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
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • 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
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/631—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine
    • H10K85/636—Amine compounds having at least two aryl rest on at least one amine-nitrogen atom, e.g. triphenylamine comprising heteroaromatic hydrocarbons as substituents on the nitrogen atom
    • 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
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
    • H10K85/6572—Polycyclic condensed heteroaromatic hydrocarbons comprising only nitrogen in the heteroaromatic polycondensed ring system, e.g. phenanthroline or carbazole
    • 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
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • 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
    • C09K2211/1074—Heterocyclic compounds characterised by ligands containing more than three nitrogen atoms as heteroatoms
    • 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
    • H10K50/125—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers specially adapted for multicolour light emission, e.g. for emitting white light
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02B—CLIMATE CHANGE MITIGATION TECHNOLOGIES RELATED TO BUILDINGS, e.g. HOUSING, HOUSE APPLIANCES OR RELATED END-USER APPLICATIONS
    • Y02B20/00—Energy efficient lighting technologies, e.g. halogen lamps or gas discharge lamps

Definitions

  • the present invention relates to a white organic fluorescent compound, and more particularly to a white organic fluorescent compound that has a quinacridone skeleton, is robust, has good processability, and emits white light with high luminance.
  • the white organic fluorescent compound represented by the formula (1) has been studied as a good light-emitting material for EL devices having a quinacridone skeleton.
  • R 1 and R 2 are disclosed for R 1 and R 2 .
  • R 1 is a hydrogen atom, an alkyl group, a benzyl group, etc.
  • Force R 2 is an alkyl group.
  • Patent Document 1 and Patent Document 2 See Patent Document 1 and Patent Document 2.
  • the already known white organic fluorescent compounds having the above-mentioned characteristic groups still have difficulties in luminance and lifetime as EL devices. In particular, there was a problem in stably attaching the EL element on the substrate.
  • Patent Document 1 JP 2003-192684 A
  • Patent Document 2 JP 2003-203780 A
  • a first means for solving the above problem is a white organic fluorescent compound represented by the formula (1).
  • R 1 represents a benzyl group in which a hydrogen atom of a phenyl group is substituted with an alkyl group having 2 to 5 carbon atoms.
  • R 2 represents any of a hydrogen atom, an alkyl group, an aryl group or an aryl group.
  • a second means for solving the above problem is a white organic fluorescent compound represented by the above formula (1).
  • R 1 represents a naphthomethyl group in which a hydrogen atom of a naphthyl group is replaced with an alkyl group having 1 to 5 carbon atoms.
  • R 2 represents a hydrogen atom, an alkyl group, an aryl group, or an arylenorequinolene group! /.
  • a third means for solving the above problem is a white organic fluorescent compound represented by the above formula (1).
  • R 1 represents an anthrylmethyl group in which a hydrogen atom of an anthryl group (anthryl group) is substituted with an alkyl group having 1 to 5 carbon atoms.
  • R 2 represents a hydrogen atom, an alkyl group, an aryl group or an aryl group.
  • R 1 and R 2 may be the same group or different groups. Further, the substituent bonded to the phenyl group, naphthyl group and anthryl group in R 1 may be one alkyl group or two or more alkyl groups. Further, when there are two or more substituted alkyl groups, they may be the same or different substituents.
  • a white organic phosphor compound suitable as a light-emitting material for high-luminance, high-purity white and long-life EL elements that can be used for various white light emitters including organic EL elements and the like. Can provide. In particular, it is well suited for the production of stable EL elements that adhere well on the substrate as EL elements.
  • FIG. 1 is an IR chart of compound (13) in Example 1.
  • FIG. 2 is an NMR chart of the compound (13) in Example 1.
  • FIG. 3 shows the fluorescence spectrum of the white organic fluorescent compound (14) of Example 1. is there.
  • FIG. 4 is an IR chart of the compound (15) in Example 2.
  • FIG. 5 is an NMR chart of the compound (15) in Example 2.
  • FIG. 6 is an IR chart of the white organic fluorescent compound (16) in Example 2.
  • FIG. 7 is an NMR chart of white organic fluorescent compound (16) in Example 2.
  • FIG. 8 is a graph showing the fluorescence spectrum of the white organic fluorescent compound (16) of Example 2.
  • FIG. 9 is an IR chart of the compound (19) in Example 3.
  • FIG. 10 is an NMR chart of the compound (19) in Example 3.
  • FIG. 11 is an IR chart of the compound (20) in Example 3.
  • FIG. 12 is an NMR chart of the compound (20) in Example 3.
  • FIG. 13 is an IR chart of the compound (21) in Example 3.
  • FIG. 14 is an IR chart of the white organic fluorescent compound (22) in Example 3.
  • FIG. 15 is a graph showing the fluorescence spectrum of the white organic fluorescent compound (22) of Example 3.
  • FIG. 16 is an explanatory view showing an example of an organic EL element.
  • a compound having a quinacridone skeleton such as a white organic fluorescent compound represented by the general formula (1), can be used as an EL device.
  • some of R 1 and R 2 have already been used.
  • Such groups are disclosed.
  • the present inventors obtained a particularly excellent white organic fluorescent compound for EL devices by optimally selecting the characteristic group R 1 bonded to the nitrogen atom of quinacridone. I was able to.
  • the quinacridone skeleton was distorted by utilizing steric hindrance and electron donating property in the molecule, and the luminescence function was adjusted.
  • the inventors have invented a white light-emitting material that enhances light emission on the low wavelength side, which is relatively difficult to emit light, and sufficiently develops red light emission and is well-balanced or has adjusted light emission characteristics.
  • the white organic fluorescent compound represented by the formula (1) according to the present invention has a quinacridone skeleton represented by the formula (3).
  • This quinacridone is well known as a pigment called Pigment Violet 19, which is synthesized by, for example, condensation, ring closure and acidification using, for example, jetyl succinyl succinate and arrin as main raw materials. Therefore, the white organic fluorescent compound according to the present invention is also excellent in fastness, weather resistance, light resistance and heat resistance.
  • R 1 is a benzyl group in which a hydrogen atom of a phenyl group is substituted with an alkyl group having 2 to 5 carbon atoms, or a hydrogen atom of a naphthyl group is an alkyl group having 1 to 5 carbon atoms.
  • Two R 1 may be the same or different.
  • R 1 is a substituted benzyl group
  • the hydrogen atom of the phenyl group is substituted with an alkyl group having 2 to 5 carbon atoms.
  • This alkyl group having 2 to 5 carbon atoms is a characteristic group selected from an ethyl group, a propyl group, a butyl group, and a pentyl group.
  • the propyl group, butyl group and pentyl group may each be linear or branched. Branched characteristic groups such as isopropyl and tertiary butyl groups are preferred.
  • the substitution position on the phenyl group may be anywhere, but the ortho and para positions are suitable. This is probably because the electron donating effect of the benzyl group is strong.
  • Two or more alkyl groups may be substituted for the hydrogen atom of the phenyl group. In this case, the same or different substituents may be used.
  • the quinacridone skeleton As described above, by selecting a characteristic group that binds to the nitrogen atom of the quinacridone skeleton, the quinacridone skeleton, or even the entire molecule, has a steric or electronic state due to steric hindrance or electron donating properties in the molecule.
  • the light emission function changes. As a result, light emission on the low wavelength side, which is considered to be relatively difficult to emit light, is increased, so that red light emission is sufficiently developed and a balanced white light-emitting material can be obtained.
  • the reason why the substituent alkyl group is 5 or less carbon atoms is that if the alkyl group becomes too large, the light emitting device per molecule Even if the performance is the same, the light emitting function per weight will be reduced. In addition, if the molecular weight is too large, production and handling as a compound becomes difficult.
  • R 1 is a substituted naphthomethyl group
  • the hydrogen atom of the naphthyl group is a naphthomethyl group substituted with an alkyl group having 1 to 5 carbon atoms.
  • This alkyl group having 1 to 5 carbon atoms is a characteristic group in which methyl, ethyl, propyl, butyl, and pentyl groups are also selected.
  • the substituted naphthomethyl group may be either (X naphthomethyl group or ⁇ -naphthomethyl group.
  • the alkyl group as a substituent is a propyl group, a butyl group, or a pentyl group, each is linear or branched.
  • the substitution position of the alkyl group to the naphthyl group may be anywhere, and more than two alkyl groups may be substituted for the hydrogen atom of the naphthyl group.
  • the quinacridone skeleton is distorted due to steric hindrance and electron donating properties in the molecule, and As a result, the light emission on the low wavelength side, which is considered to be relatively difficult to emit light, increases, and the red light emission is fully developed and balanced.
  • the alkyl group as a substituent is 5 or less carbon atoms, if the alkyl group is too large, the light emission function per weight will drop even if the light emission function per molecule is the same. In addition, if the molecular weight is too large, manufacture and handling as a compound becomes difficult.
  • R 1 is a substituted anthrylmethyl group
  • the hydrogen atom of the anthryl group is an anthrylmethyl group substituted with an alkyl group having 1 to 5 carbon atoms.
  • This alkyl group having 1 to 5 carbon atoms is a characteristic group selected from a methyl group, an ethyl group, a propyl group, a butyl group, and a pentyl group.
  • the alkyl group as a substituent is a propyl group, a butyl group, or a pentyl group, each may be linear or branched.
  • the substitution position of the alkyl group to the anthryl group may be anywhere.
  • Two or more alkyl groups may be substituted for the hydrogen atom of the anthryl group.
  • the same substituent or different substituents may be used.
  • the quinacridone skeleton is distorted due to steric hindrance and electron donating properties in the molecule, and the luminescence function changes . This makes it relatively difficult to emit light. Therefore, red light emission is sufficiently developed and a balanced white light emitting material can be obtained.
  • the reason why the substituent alkyl group is 5 or less carbon atoms is that if the alkyl group becomes too large, the light emitting function per weight will be lowered even if the light emitting function per molecule is the same. If the molecular weight is too large, it is difficult to manufacture and handle as a compound.
  • the two characteristic groups R 2 are each a hydrogen atom, an alkyl group, an aryl group or an aryl group, each of which is the same group May be different groups.
  • the alkyl group include an alkyl group having 1 to 30 carbon atoms, and a lower alkyl group having 1 to 5 carbon atoms such as a methyl group, an ethyl group, and a propyl group is particularly preferable.
  • the two characteristic groups R 2 may be the same or different.
  • R 2 is an aryl group
  • the aryl group includes a phenyl group, a naphthyl group, an anthryl group, a biphenyl group, and a substituent such as an alkyl group or an alkoxy group bonded to these aromatic rings. Examples thereof include a p-tolyl group and a p-alkoxyphenol group.
  • the arylalkyl group includes a benzyl group, a 1-phenylethyl group, a 2-phenylethyl group, a 1-phenylpropyl group, a 2-phenylpropyl group, 3 Examples thereof include a phenylpropyl group and a 4-phenylbutyl group.
  • the phenyl group may be further substituted with a substituent such as an alkyl group.
  • Preferred arylalkyl groups are benzyl group and p-methylbenzyl group.
  • the white organic fluorescent compound represented by the formula (1) of the third invention of the first force is By having the substituent of R 2 , solubility in a solvent is improved, and therefore, coating property by dissolving in an appropriate solvent is improved, and sublimation temperature is lowered, so that workability by vapor deposition is improved. Furthermore, the compatibility with the polymer compound is improved, so that it can be included in the polymer film. In particular, by selecting R 1 , it is an excellent white organic fluorescent compound with particularly improved emission luminance, sublimation temperature, and compatibility with a polymer compound when an EL device is obtained.
  • the white organic fluorescent compound represented by the formula (1) can be produced, for example, according to the following reaction formula.
  • R is a lower alkyl group such as a methyl group or an ethyl group
  • R 1 and R 2 are the same characteristic groups as described above.
  • the above reaction formula is, for example, dialkyl 2,5 dihydroxy 1,4-cyclohexadiene 1,4-dicarboxylate (compound (4) in the above reaction formula) and a compound (5) such as 3-amino-9 alkyl strength rubazole.
  • the reaction proceeds by heating in an appropriate solvent.
  • a dehydration reaction proceeds to obtain a compound (6) crosslinked with an amino group.
  • an appropriate dehydrating agent such as concentrated sulfuric acid can be used.
  • R 2 When R 1 is hydrogen, the dehydrogenation reaction product (7) is, for example, I ⁇ HaU in DMF, where HaL represents a halogen atom. ) Can be reacted to alkylate the dehydrogenation reaction product (7).
  • the ring closure reaction is carried out by heating in an appropriate solvent, preferably in the presence of an organic acid catalyst such as sulfuric acid or p-toluenesulfonic acid, in an appropriate solvent such as dichlorobenzene in an inert high-boiling organic solvent. It progresses by heating with.
  • an organic acid catalyst such as sulfuric acid or p-toluenesulfonic acid
  • dichlorobenzene in an inert high-boiling organic solvent.
  • the compound power represented by (8) in the above reaction formula is the white organic fluorescent compound according to the present invention represented by the above formula (1).
  • the white organic fluorescent compound according to the present invention emits light in the region of 400 to 700 nm and can be used for an organic EL device capable of emitting white light.
  • the organic EL device using the white organic fluorescent compound of the present invention comprises an ITO anode, polybulur rubazole (PVK), 2- (4 tert butylphenol) 5- (4-biphenyl) -1, 3 4, 4 Oxadiazole and a white organic fluorescent compound-containing light emitting layer and a cathode formed on the surface of the light emitting layer may be used.
  • ITO anode polybulur rubazole (PVK)
  • 2- (4 tert butylphenol) 5- (4-biphenyl) -1, 3 4, 4 Oxadiazole and a white organic fluorescent compound-containing light emitting layer and a cathode formed on the surface of the light emitting layer may be used.
  • the energy level is conduction band power It is a phenomenon in which energy is released as light when returning to the child band.
  • This organic EL element can employ various types of structures as long as it has a light emitting layer containing a white organic fluorescent compound according to the present invention between an anode and a cathode.
  • this organic EL element for example, as shown in FIG. 16, the transparent electrode 3 formed on the surface of the transparent substrate 2 and the white electrode according to the present invention formed on the surface of the transparent electrode 3 are used.
  • a single-layer organic light emitting device comprising a light emitting layer 4 containing an organic fluorescent compound and a cathode 5 formed on the surface of the light emitting layer 4 can be mentioned.
  • the light emitting layer can be a deposited layer formed by depositing a white organic fluorescent compound represented by the above formula (1).
  • an electron transporting material that transports electrons between the anode and the cathode, the white organic fluorescent compound according to the present invention, and a hole transporting hole.
  • a single-layer organic light-emitting device having a light-emitting layer containing both a hole-transporting polymer, a hole-transporting layer containing a hole-transporting substance between the anode and the cathode formed on the substrate, and the present invention A two-layer organic low-molecular light-emitting device formed by laminating such a white organic fluorescent compound-containing electron transporting light emitting layer (for example, a hole transporting layer between an anode and a cathode, and a white color according to the present invention as a guest dye)
  • the organic EL element can usually be formed on a substrate.
  • this substrate include transparent substrates such as glass and plastic.
  • the anode can be made of various materials as long as it has a large work function and is transparent, and holes can be injected into the film by applying a voltage.
  • ITO indium gallium
  • Inorganic transparent conductive materials such as O, SnO, ZnO, CdO, etc., and their compounds, and poly
  • This anode is formed on the substrate by chemical vapor deposition, spray pie-lysis, vacuum deposition, electron beam deposition, sputtering, ion beam sputtering, ion plating, ion assisted deposition, It can be formed by other methods.
  • the cathode employs a material having a small work function, and may be formed of a single metal or a metal alloy such as MgAg, aluminum alloy, and calcium metal.
  • a preferred cathode is an alloy electrode of aluminum and a small amount of lithium.
  • the cathode can be easily formed on the surface of the organic layer including the light emitting layer formed on the substrate, for example, by a vapor deposition technique.
  • Examples of the electron transporting substance include 2- (4-tert-butylphenol) -5- (4-biphenyl) 1,3,4-oxadiazole derivatives and the like, and 2, 5 bis (1 naphthyl) 1,3,4 oxadiazole, 2,5 bis (5′-tert-butyl-2′-benzoxazolyl) thiophene, and the like.
  • a metal complex material such as quinolinol aluminum complex (Alq3) or benzoquinolinol beryllium complex (Bebq2) can be preferably used.
  • Examples of the hole transport material include triphenylamine compounds such as N, N'-diphenyl-N, N, 1di (m tolyl) 1benzidine (TPD), and ⁇ -NPD, hydrazone compounds, Examples include stilbene compounds, heterocyclic compounds, and ⁇ -electron starburst hole transport materials.
  • the organic layer in the organic EL element can be formed by any one of a coating method such as a spin casting method, a coating method, a dip method, and a vapor deposition method. Whichever of the coating method and the vapor deposition method is adopted, it is preferable to interpose a buffer layer between the electrode and the organic layer. Forming the buffer layer formed between the cathode and the organic layer; Examples of materials that can be used include, for example, alkali metal compounds such as lithium fluoride, alkaline earth metal compounds such as magnesium fluoride, acid compounds such as acid aluminum, 4, 4, 1 bis carbazole biphenol (Cz-TPD).
  • a coating method such as a spin casting method, a coating method, a dip method, and a vapor deposition method. Whichever of the coating method and the vapor deposition method is adopted, it is preferable to interpose a buffer layer between the electrode and the organic layer. Forming the buffer layer formed between the cathode and the organic layer; Examples of materials that can be used include
  • m-MTDA TA (4, 4 ,, 4 "-tris (3-methylphenol-lamino) is used as a material for forming a buffer layer formed between an anode such as ITO and an organic layer.
  • anode such as ITO and an organic layer.
  • Triphenylamine Triphenylamine
  • lid opening polyarine
  • polythiophene derivatives polythiophene derivatives
  • inorganic oxides such as molybdenum oxide, ruthenium oxide, vanadium oxide, and lithium fluoride.
  • the electron-transporting light-emitting layer in this light-emitting element is usually 50 to 80% polyvinyl carbazole (PVK), 5 to 40% of an electron-transporting light-emitting agent, and the white organic fluorescent material according to the present invention. When formed with 0.01 to 20% (by weight) of compound, white light emission occurs with high brightness.
  • the hole transporting polymer include polyvinylcarbazole and poly (3-alkylenephene).
  • the organic layer preferably contains rubrene as a sensitizer, and particularly preferably contains rubrene and Alq3.
  • the organic EL device using the white organic fluorescent compound according to the present invention can be generally used as, for example, a direct current drive device, and can also be used as a pulse drive device and an AC drive device. Can be used.
  • the white organic fluorescent compound according to the present invention is further used in the display field such as a monochrome display and a color display, and in the lighting field such as a light sign, a direct-view sign, indirect illumination, and an LCD backlight.
  • X represents a 4-methyl-1-naphthomethyl group (CH C H CH—).
  • X represents a 4-methyl-1-naphthomethyl group (CH C H CH-).
  • the white organic fluorescent compound (14) was dissolved in mixed xylene to a concentration of lOmgZL to prepare a sample solution.
  • This sample solution was loaded into an F-4500 spectrofluorometer manufactured by Shimadzu Corporation, and the fluorescence spectrum was measured under the following conditions. The resulting fluorescent spectrum is shown in FIG.
  • the white organic fluorescent compound obtained in this example is 400 700 nm. Fluorescence can be seen, covering the entire area.
  • Example 1 The compound represented by the manufactured formula (12) in Example 1 5. 0 g of (8. 49 X 10- 3 mol) was placed in ⁇ bottle 1000 ml, 4-t-butylbenzyl bromide 9. 3 g (5 09 X 10 _2 mol) was added, and then 400 ml of N, N-dimethylformamide (DMF) was added. Using a silicone oil bath, the pressure bottle was heated to 160 ° C with stirring and allowed to react for 20 hours. After completion of the reaction, the mixture was cooled to room temperature, concentrated using an evaporator, poured into ice water, and neutralized with sodium hydroxide. Using a separatory funnel, black mouth form extraction was performed three times, and water washing was performed twice.
  • DMF N, N-dimethylformamide
  • Y represents a 4-tbutylbenzyl group (4- (CH 3) CC H CH—).
  • Y represents a 4-tbutylbenzyl group (4- (CH) CC H CH-).
  • This white organic fluorescent compound-containing solution was made sufficiently uniform by irradiating ultrasonic waves with an ultrasonic cleaner (US-2, manufactured by SND Corporation) for 20 minutes.
  • an ultrasonic cleaner US-2, manufactured by SND Corporation
  • an ITO substrate 50 ⁇ 50 mm, Sanyo Vacuum Industries Co., Ltd.
  • UV irradiation was performed for 30 seconds with a UV irradiation device (manufactured by M'D Excimer, wavelength 172 nm) for cleaning.
  • the prepared white organic fluorescent compound-containing solution is dropped onto an ITO substrate that has been cleaned and dried using a spin coater (Mikasa Co., Ltd., 1H-D7), and the rotational speed is 1,500 rpm and the rotational time is A film was formed by spin coating in 3 seconds.
  • An EL device was manufactured. The luminance and chromaticity of this EL element were measured with a spectroradiometer SR-3 manufactured by Topcon Corporation.
  • the voltage was 12.5 V
  • the current was 18.8 mA
  • the luminance was 12000 CdZm 2
  • the chromaticity X was 0.
  • the white organic fluorescent compound (16) was dissolved in mixed xylene to a concentration of lOmgZL to prepare a sample solution.
  • This sample solution was loaded into an F-4500 spectrofluorometer manufactured by Shimadzu Corporation, and the fluorescence spectrum was measured under the following conditions. The resulting fluorescent spectrum is shown in FIG.
  • the white organic fluorescent compound obtained in this example is 400 to 700 nm. Fluorescence can be seen, covering the entire area. In particular, there is a large peak at 562 nm.
  • X represents a 4-tbutylbenzyl group (4- (CH) CC H CH-).
  • the solid obtained was washed with methyl alcohol, acetone and petroleum ether cooled to 5 ° C., and then dried in vacuo to obtain a solid, and 1.0 g of the solid was collected using a Soxhlet extraction apparatus. Extracted with 250 ml of silene over 24 hours, concentrated to dryness using an evaporator after completion of extraction, and the resulting solid was washed with petroleum ether and vacuum dried to obtain 0.5 g of a black powder.
  • Fig. 14 shows the IR chart of the body
  • Fig. 15 shows the fluorescence spectrum measured in the same manner as in Example 1. Indicated.
  • the solid was filed white organic fluorescent compounds having the structure shown by the formula (22).
  • X represents a 4-tbutylbenzyl group (4- (CH) CC H CH-).
  • the white organic fluorescent compound (22) obtained in this example shows fluorescence emission at 400 to 700 nm and covers the entire region. In particular, there are large peaks not only on the short wavelength side but also on the long wavelength side of 555 nm and 595 nm.
  • the white organic fluorescent compound of the present invention can be used to emit white light by an organic EL element, a display, a lighting device, or the like.
  • the white organic fluorescent compound can be made into a light emitting element capable of emitting blue light, red light and green light by spectroscopic analysis using a prism, and further, a full color display can be performed using a color filter. It can also be used for LCD backlights.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Est décrit un composé organique fluorescent blanc qui est un composé unique émettant de la lumière blanche de luminance supérieure. Un tel composé organique fluorescent blanc est rapide, excellent de par son aptitude au traitement et peut être utilisé pour divers corps luminescents blancs tels que des dispositifs EL organiques. Est spécifiquement décrit un composé organique fluorescent blanc qui se caractérise du fait qu'il est représenté par la formule (1) ci-dessous. Dans la formule (1), R1 représente un groupe alkylbenzyle en C2 à C5, un groupe alkylnaphtométhyle en C1 à C5 ou un groupe alkylanthrylméthyle en C1 à C5 ; et R2 représente un atome d’hydrogène, un groupe alkyle, un groupe aryle ou un groupe arylalkyle. (1)
PCT/JP2005/010910 2004-06-25 2005-06-15 Composé organique fluorescent blanc WO2006001198A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
JP2004-188501 2004-06-25
JP2004188501 2004-06-25

Publications (1)

Publication Number Publication Date
WO2006001198A1 true WO2006001198A1 (fr) 2006-01-05

Family

ID=35781702

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/JP2005/010910 WO2006001198A1 (fr) 2004-06-25 2005-06-15 Composé organique fluorescent blanc

Country Status (2)

Country Link
TW (1) TW200602477A (fr)
WO (1) WO2006001198A1 (fr)

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1187059A (ja) * 1997-09-04 1999-03-30 Mitsui Chem Inc 有機電界発光素子
WO2003062237A1 (fr) * 2002-01-18 2003-07-31 Hirose Engineering Co., Ltd. Compose emettant la lumiere blanche, dispositif d'eclairage emettant la lumiere blanche et dispositif el organique emettant la lumiere blanche

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
JPH1187059A (ja) * 1997-09-04 1999-03-30 Mitsui Chem Inc 有機電界発光素子
WO2003062237A1 (fr) * 2002-01-18 2003-07-31 Hirose Engineering Co., Ltd. Compose emettant la lumiere blanche, dispositif d'eclairage emettant la lumiere blanche et dispositif el organique emettant la lumiere blanche

Also Published As

Publication number Publication date
TW200602477A (en) 2006-01-16

Similar Documents

Publication Publication Date Title
JP3109896B2 (ja) 有機エレクトロルミネッセンス素子
JP3724833B2 (ja) 有機エレクトロルミネッセンス素子
JP5274459B2 (ja) 有機エレクトロルミネッセンス素子用材料及び有機エレクトロルミネッセンス素子
JP2651233B2 (ja) 薄膜有機ｅｌ素子
KR101115156B1 (ko) 벤조플루오란텐 화합물 및 이 화합물을 사용한 유기 발광소자
WO2003080761A1 (fr) Materiau pour element organique electroluminescent et element organique electroluminescent l'utilisant
JP5186173B2 (ja) 有機エレクトロルミネッセンス素子用材料および化合物
JP2003272857A (ja) 白色系有機エレクトロルミネッセンス素子
JPH1088121A (ja) 有機エレクトロルミネッセンス素子材料およびそれを使用した有機エレクトロルミネッセンス素子
KR101424266B1 (ko) 유기 전계 발광소자
US20050118454A1 (en) Luminescent compound emitting white light, illuminator and organic el element emitting white light
JP3798985B2 (ja) 単一化合物による白色発光照明装置及び白色発光有機ｅｌ素子
US20060152143A1 (en) White-emitting compounds, process for the production thereof, and white-emitting devices
WO2006001198A1 (fr) Composé organique fluorescent blanc
JP2007099723A (ja) 白色有機蛍光化合物及び発光素子
JPH05247459A (ja) 有機エレクトロルミネッセンス素子
EP1475372A1 (fr) Compose de type rouge nil emettant de la lumiere rouge, son procede de production et element luminescent faisant appel a ce compose
JP3109894B2 (ja) 有機エレクトロルミネッセンス素子
JP2003192684A (ja) 白色有機蛍光化合物
US20060004201A1 (en) White organic fluorescent compound
JP2002249469A5 (fr)
JP2005071773A (ja) フルカラー画像表示装置
US20050089719A1 (en) White light-emitting compound, process for producing the same, and luminescent element utilizing the same
JP2670121B2 (ja) 有機薄膜エレクトロルミネッセンス素子
JP2004035447A (ja) フッ化アルキル基含有スチルベン系青色発光化合物及び発光素子

Legal Events

Date Code Title Description
AK Designated states

Kind code of ref document: A1

Designated state(s): AE AG AL AM AT AU AZ BA BB BG BR BW BY BZ CA CH CN CO CR CU CZ DE DK DM DZ EC EE EG ES FI GB GD GE GH GM HR HU ID IL IN IS JP KE KG KM KP KR KZ LC LK LR LS LT LU LV MA MD MG MK MN MW MX MZ NA NG NI NO NZ OM PG PH PL PT RO RU SC SD SE SG SK SL SM SY TJ TM TN TR TT TZ UA UG US UZ VC VN YU ZA ZM ZW

AL Designated countries for regional patents

Kind code of ref document: A1

Designated state(s): GM KE LS MW MZ NA SD SL SZ TZ UG ZM ZW AM AZ BY KG KZ MD RU TJ TM AT BE BG CH CY CZ DE DK EE ES FI FR GB GR HU IE IS IT LT LU MC NL PL PT RO SE SI SK TR BF BJ CF CG CI CM GA GN GQ GW ML MR NE SN TD TG

121 Ep: the epo has been informed by wipo that ep was designated in this application
NENP Non-entry into the national phase

Ref country code: DE

WWW Wipo information: withdrawn in national office

Country of ref document: DE

122 Ep: pct application non-entry in european phase
NENP Non-entry into the national phase

Ref country code: JP