WO2002102925A1 - Materiau fluorescent polymerique, procede de production, et element luminescent polymerique - Google Patents

Materiau fluorescent polymerique, procede de production, et element luminescent polymerique Download PDF

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Publication number
WO2002102925A1
WO2002102925A1 PCT/JP2001/005219 JP0105219W WO02102925A1 WO 2002102925 A1 WO2002102925 A1 WO 2002102925A1 JP 0105219 W JP0105219 W JP 0105219W WO 02102925 A1 WO02102925 A1 WO 02102925A1
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group
polymer
layer
light emitting
light
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PCT/JP2001/005219
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English (en)
Japanese (ja)
Inventor
Shuji Doi
Takanobu Noguchi
Yoshiaki Tsubata
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Sumitomo Chemical Company, Limited
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Priority to JP2000384951A priority Critical patent/JP4940493B2/ja
Application filed by Sumitomo Chemical Company, Limited filed Critical Sumitomo Chemical Company, Limited
Priority to US10/480,996 priority patent/US7357990B2/en
Priority to PCT/JP2001/005219 priority patent/WO2002102925A1/fr
Priority to DE10197249T priority patent/DE10197249T5/de
Publication of WO2002102925A1 publication Critical patent/WO2002102925A1/fr

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    • 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
    • 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
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/114—Poly-phenylenevinylene; Derivatives thereof
    • 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
    • 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
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene

Definitions

  • the present invention relates to a method for producing a polymer phosphor and a polymer light-emitting device using the same (hereinafter, may be referred to as a polymer LED). '
  • An object of the present invention is to provide a polymer phosphor excellent in solubility, a method for producing the polymer phosphor, and a high-performance polymer LED that can be driven with low voltage and high efficiency by using the polymer phosphor. It is in.
  • the present inventors have conducted intensive studies to solve the above-mentioned problems. As a result, by contacting a specific polymer fluorescent substance with an alkali, the solubility of the polymer fluorescent substance in an organic solvent has been improved, and the polymer fluorescent substance has been improved. The present inventors have found that a high-performance polymer LED that can be driven at a low voltage and with high efficiency can be obtained by using a body, and have led to the present invention.
  • the present invention 1) having fluorescence in the solid state, the number average molecular weight in terms of polystyrene is 1 0 4 to 1 0 8, and alkali crude polymeric fluorescent substance containing a repeating unit represented by the following formula (1) one or more
  • the present invention relates to a method for producing a polymeric fluorescent substance, which includes a step of contacting the polymeric fluorescent substance.
  • a ri is an arylene group or a heterocyclic compound group, and is unsubstituted or has one or more substituents. Is also good.
  • 1 1 ⁇ Pi 1 2 each independently represent a hydrogen atom, an alkyl group, Ariru group, a group selected from the group consisting of heterocyclic compound group and Shiano group.
  • the aryl group and the heterocyclic compound group may further have a substituent.
  • n is 0 or 1.
  • the present invention relates to 2) a polymeric fluorescent substance that can be produced by the production method of 1) above.
  • the present invention also provides 3) a polymer light-emitting device having at least a light-emitting layer between a pair of anodes and cathodes, at least one of which is transparent or translucent, wherein the light-emitting layer is as described in 2) above.
  • the present invention relates to a polymer light emitting device including a molecular phosphor.
  • the present invention relates to 4) a planar light source using the polymer light-emitting device of the above 3).
  • the present invention relates to 5) a segment display device using the polymer light-emitting device of the above 3).
  • the present invention relates to 6) a dot matrix display device using the polymer light emitting device of the above 3).
  • the present invention relates to 7) a liquid crystal display device using the polymer light-emitting device according to 3) as a backlight.
  • the method for producing a polymeric fluorescent substance of the present invention has fluorescence in a solid state, a polystyrene equivalent number average molecular weight of 10 4 to 10 8 , and one type of a repeating unit represented by the following formula (1).
  • the method is characterized in that it includes a step of contacting the crude polymer fluorescent material containing the above with an aluminum alloy. -Ar!-(CR ⁇ CRs) n- (1)
  • the organic solvent that can be used in the production method of the present invention is not particularly limited as long as it can dissolve the crude polymer fluorescent substance. In order to perform the treatment, it is preferable that the solvent is sufficiently dissolved. Therefore, it is preferable that the solvent be a good solvent for the crude polymer fluorescent substance.
  • Examples of good solvents for the crude polymer fluorescent substance include chloroform-form, dichloromethane, dichloroethane, tetrahydrofuran, toluene, xylene, mesitylene, tetralin, decalin, ⁇ -butylbenzene, dioxane and the like.
  • these solvents can usually be dissolved in an amount of 0.1% by weight or more.
  • the alkali used in the production method of the present invention sigma> 1 & value preferably der shall of 10 or more.
  • alkali examples include metal alkoxide, metal hydroxide, metal amide compound, metal hydride compound, ammonia, and amines.
  • the metal hydroxides include LiOH, NaOH, KOH and the like.
  • metal hydride compounds include Li H, NaH, KH and the like.
  • the amines include triethylamine, pyridine, 4-dimethylaminopyridine, diazabisic oral decane, and the like.
  • L i O (t_C 4 H 9 ), Na O (t-C 4 H 9 ), KO (t-C 4 H 9 ), L i N (t C 3 H 7) 2, Na N (i one C 3 H 7) 2, KN (i one C 3 H 7) 2, ammonia, Amin are preferred.
  • ammonia and triethylamine are more preferable in that the fluorescence intensity becomes stronger, and ammonia is particularly preferable because it has high volatility and hardly remains after the treatment. preferable.
  • the method for producing a polymeric fluorescent substance of the present invention includes a step of bringing the crude polymeric fluorescent substance into contact with an alkali. This step may be included twice or more. In the step of bringing the crude polymer fluorescent substance into contact with the alkali, the crude polymer fluorescent substance dissolved in an organic solvent is preferably brought into contact with an alkali in view of the contact efficiency.
  • Examples of the method of contacting with an alkali include: (a) a method in which an alkali is directly added to a solution in which a crude polymer fluorescent substance is dissolved; (b) a solution in which an alkali is dissolved in a solvent to dissolve a coarse polymeric fluorescent substance (C) a method in which a solution in which a crude polymer fluorescent substance is dissolved is added to a solution in which the polymer is dissolved, and (d) a method in which the crude polymer fluorescent substance is dissolved in a solvent in which the polymer is dissolved. And a method of dispersing the body.
  • the solvent for dissolving the alkali may be an organic solvent or water.
  • the solvent in which the solvent is dissolved may be a solvent that is uniformly mixed with the dissolved organic solvent, or may be a solvent that is not uniformly mixed.
  • the same organic solvent as that in which the crude polymer fluorescent material is dissolved is preferred.
  • the contact efficiency between the alkali and the polymeric fluorescent substance can be improved by stirring and shaking the solution as necessary.
  • the time for contact with the alkali is not particularly limited, but is usually 30 minutes or more and 20 hours or less, preferably 1 hour or more and 20 hours or less in order to obtain a sufficient solubility improving effect.
  • the temperature for contacting with anorecali is usually from 10 ° C. to 200 ° C., and preferably from room temperature to less than the boiling point of the solvent. Although it depends on the solvent used, it is practically more preferable that the temperature is 30 ° C. or more and 150 ° C. or less, and it is more preferable that the temperature is 50 ° C. or more and 100 ° C. or less. However, when using a highly volatile solvent such as ammonia, treatment at around room temperature is preferred.
  • the treatment it is preferable to seal in an inert atmosphere in order to suppress the deterioration of the polymer fluorescent substance, and it is preferable to shield the light so that light of a wavelength absorbed by the polymer fluorescent substance solution is not irradiated. .
  • the step of bringing the crude high molecular weight phosphor into contact with an alkali may be performed continuously without separating the step of synthesizing the coarse high molecular weight phosphor.
  • a crude polymer fluorescent substance that exists as a solution is not separated as a precipitate, And the like.
  • the production method of the present invention may include, as necessary, neutralization, washing, reprecipitation, drying, and other steps in addition to the step of bringing into contact with an alkali.
  • the step of contacting the polymer phosphor it is preferable to provide a step of removing the polymer phosphor from the polymer phosphor.
  • a neutralization treatment it is necessary to carry out a neutralization treatment and then to wash sufficiently, or to wash sufficiently using a solvent that can dissolve the alcohol well.
  • the alkali can also be removed by dissolving the polymeric fluorescent substance obtained by bringing it into contact with an alkali and reprecipitating it with a solvent and a poor solvent.
  • a solvent and a poor solvent In order to remove highly volatile alcohol such as ammonia, drying under reduced pressure or heating in an inert atmosphere may be used.
  • Polymeric fluorescent substance of the present invention are typically, a molecular weight of 10 4 to polystyrene standards
  • the total number of those repeating structures varies depending on the repeating structures, their ratio, and the processing method after combining.
  • the total number of the repeating structures is preferably from 20 to 10,000, more preferably from 30 to 10,000, and particularly preferably from 50 to 5,000, from the viewpoint of film formability.
  • the polymer fluorescent substance of the present invention When used as a light emitting material for a polymer LED, its purity affects the light emitting properties.Therefore, after polymerization or alkali treatment, purification treatment such as reprecipitation purification, separation by chromatographic method, etc. should be performed. Is preferred.
  • the crude polymer fluorescent substance has fluorescence in a solid state, has a number average molecular weight of 10 4 to 10 8 in terms of polystyrene, and contains at least one kind of the repeating unit represented by the above formula (1).
  • the total amount of the repeating units is not more than 100 Mo ⁇ ⁇ % 10 mole 0/0 or more of the total repeating units, in order to obtain a sufficient effect of contacting with the alkali is not less than 30 mol% to 100 mol 0/0 or less Is more preferable, and it is further preferable that it is 50 mol% or more and 100 mol% or less.
  • Ar i is an arylene group or a heterocyclic compound group.
  • the arylene group usually has 6 to 60 carbon atoms in the main chain
  • the heterocyclic compound group usually has 4 or more carbon atoms in the main chain. It consists of 60 or less.
  • "number of carbon atoms contained in the main chain portion" also Alpha gamma iota can have a substituent group, the number of carbon atoms of Alpha gamma iota is that no such include the number of carbon atoms of the substituent means.
  • Ar ;! may be selected so as not to impair the fluorescent properties of the polymeric fluorescent substance, and specific examples include the following divalent groups.
  • R is independently a hydrogen atom, an alkyl group, an alkoxy group, an alkylthio group, an alkylsilyl group, an alkylamino group, an aryl group, an aryloxy group, an arylalkyl group, an arylalkoxy group, an aryl group.
  • Alkenyl group It represents a group selected from the group consisting of a reelalkynyl group, an arylamino group, a heterocyclic compound group and a cyano group.
  • one structural formula has a plurality of Rs, but they may be the same or different groups, and each is independently selected.
  • Ar has a plurality of substituents, they may be the same or different.
  • the compound preferably has at least one substituent that is not a hydrogen atom, and preferably has low symmetry in the shape of the repeating unit including the substituent.
  • the alkyl group may be straight-chain, branched or cyclic, and usually has about 1 to 20 carbon atoms. Specifically, methyl, ethyl, propyl, i-propyl, butyl, i Monobutyl, t-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl, lauryl, etc.
  • a pentyl group, a hexyl group, an octyl group, a 2-ethylhexyl group, a decyl group, and a 3,7-dimethinoleoctyl group are preferred.
  • the alkoxy group may be straight-chain, branched or cyclic, and usually has about 1 to 20 carbon atoms.
  • methoxy, ethoxy, propyloxy, i-propyloxy, butoxy, i-butoxy group, t-butoxy group pentyloxy group, hexyloxy group, cyclohexyloxy group, heptyloxy group, otatyloxy group, 2-ethylhexyloxy group, nonyloxy group, decyloxy group, 3,7-dimethyloctyl
  • the alkylthio group may be linear, branched or cyclic, and usually has about 1 to 20 carbon atoms. Specifically, methylthio, ethylthio, propylthio, i-propylthio, butylthio, i —Butylthio, t-butyl ⁇ thio, pentylthio, hexylthio, cyclohexylthio, heptylthio, otatinolethio, 2-ethylhexylthio, nonylthio, decylthio, 3,71 Dimethyl otatyl thio group, lauryl thio group, etc., pentyl thio group, Hexylthio, octylthio, 2-ethylhexylthio, decylthio, and 3,7-dimethylotatylthio are preferred.
  • the alkylsilyl group may be linear, branched or cyclic, and usually has about 1 to 60 carbon atoms. Specifically, methylsilyl group, ethylsilyl group, propylsilyl group, i- propylsilyl group, butylsilyl group , I-butylsilyl, t-butylsilyl, pentylsilyl, hexylsilyl, cyclohexylsilyl, heptylsilyl, octylsilyl, 2-ethylhexylsilyl, nonylsilyl, decylsilyl, 3,7- Dimethyloctylsilyl group, laurylsilinole group, trimethylsilyl group, ethyldimethylsilyl group, propyldimethylsilyl group, i-propyldimethylsilyl group, butyldimethylsilyl group,
  • the alkylamino group may be linear, branched or cyclic, may be a monoalkylamino group or a dialkylamino group, and usually has about 1 to 40 carbon atoms. Specifically, a methylamino group, a dimethylamino group, Ethylamino, acetylamino, propylamino, i-propylamino, butylamino, i-butylamino, t-butylamino, pentylamino, hexinoleamino, cyclohexylamino, heptylamino, octylamino, 21-ethyl Hexylamino group, nonylamino group, decylamino group, 3,7-dimethyloctylamino group, laurylamino group, etc., pentylamino group, hexylamino group, octylamino group, 2-
  • Ariru group has a carbon number of usually 6-6 0 degree, specifically, phenyl group, c i ⁇ c i 2 alkoxy phenylalanine group (c i to c i 2 is the number 1 to 1 2 carbon atoms the same is true. below indicate that.), C i ⁇ C 1 2 alkylphenyl group, 1-naphthyl group, 2-naphthyl group and the like, Ji ⁇ ⁇ Ji 2 alkoxy phenylalanine groups, C i C i 2 alkylphenyl group are preferable.
  • Ariruokishi group has a carbon number of usually 6-6 0 degree, specifically, Fuweno alkoxy group, C i ⁇ C 2 alkoxy phenoxyethanol group, C i ⁇ C 1 2 alkylphenoxy groups, 1- Examples include a naphthyloxy group and a 2-naphthyloxy group;
  • a C 12 alkoxy phenoxy group and a C i C jL 2 alkyl phenoxy group are preferred.
  • ⁇ reel alkyl group has a carbon number of usually 7-6 0 degree, specifically, Hue sulfonyl one C ⁇ 1 2 alkyl group, C E ⁇ C ⁇ 2 ⁇ Honoré Koki Schiff enyl one C. 1 to C 1 2 alkyl group, C E ⁇ i 2 Arukirufue two Lou C ⁇ ! 2- alkyl group, 1-naphthyl-C 1 ⁇ 2 1 alkyl group, 2-naphthyl-C-!
  • Such as 2-alkyl group is represented example, C i ⁇ C 1 2 Arukokishifue two Lou C I ⁇ C 1 2 alkyl group, C! Le Shi preferred is ⁇ C 1 2 alkyl Fe two Lou C ⁇ C i 2 alkyl groups ,.
  • ⁇ reel alkoxy group has a carbon number of usually 7-6 0 degree, specifically, full Eniru C ⁇ Ji 1 2 alkoxy, C -C 2 alkoxy phenylalanine one C-C 1 2 alkoxy group, C to ⁇ i 2 alkylphenyl C to C 12 alkoxy group,
  • Ariruamino group has a carbon number of usually 6-6 0 C.
  • Heterocyclic compound group has a carbon number of usually 4-6 0 degree, specifically, thienyl group, C 1 ⁇ ] L 2 alkyl chain group, a pyrrolyl group, a furyl group, a pyridyl group, C! ⁇ CJ 2 such alkyl pyridyl group are exemplified, thienyl group, C ⁇ CJ 2 Al Kirucheniru group, a pyridyl group, a C ⁇ C i 2 alkyl pyridyl group are preferable.
  • R in the substituent containing an alkyl chain, they may be linear, branched, or cyclic, or a combination thereof.
  • the substituent is not linear, for example, isoamyl group, 2-ethyl Hexyl group, 3,7-dimethyloctyl group, hexyl hexyl group, 41. Examples thereof include 2- alkylcyclohexyl group and the like.
  • at least one of the substituents of Ari contains a cyclic or branched alkyl chain.
  • a plurality of Rs may be linked to form a ring.
  • R is a group containing an alkyl chain
  • the alkyl chain may be interrupted by a group containing a hetero atom.
  • the hetero atom include an oxygen atom, a sulfur atom, and a nitrogen atom.
  • the group containing a hetero atom include the following groups.
  • examples of R 3 include a hydrogen atom, an alkyl group having 1 to 20 carbon atoms, an aryl group having 6 to 60 carbon atoms, and a heterocyclic compound group having 4 to 60 carbon atoms. Further, among the examples of R, when a aryl group / heterocyclic compound group is contained in a part thereof, they may further have one or more substituents.
  • n is 0 or 1.
  • R 2 represents a group independently selected from the group consisting of a hydrogen atom, an alkyl group, an aryl group, a heterocyclic compound group and a cyano group.
  • R i and R 2 are substituents other than a hydrogen atom or a cyano group will be described.
  • the alkyl group may be straight-chain, branched or cyclic, and usually has about 1 to 20 carbon atoms. Specifically, methyl, ethyl, propyl, i-propyl, Butyl, i-butyl, t-butyl, pentyl, hexyl, cyclohexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, 3,7-dimethyloctyl A pentyl group, a hexyl group, an octyl group, a 2-ethylhexyl group, a decyl group, and a 3,7-dimethyloctyl group.
  • Ariru group has a carbon number of usually 6-6 0 degree, specifically, Fuyuniru group, C I ⁇ C ⁇ 2 alkoxy phenylalanine group, C ⁇ Ji 2 alkylphenyl group, 1 one naphthyl group, Examples thereof include a 2-naphthyl group and the like, with preference given to C 1 -C 2 i-alkoxyphenyl groups and C i -C 2 -alkylphenyl groups.
  • the heterocyclic compound group usually has about 4 to 60 carbon atoms, and specifically includes a phenyl group.
  • ⁇ Ji 2 alkyl chain group, a pyrrolyl group, a furyl group, a pyridyl group, c. 1 to C 1 2 alkyl pyridyl group are exemplified, thienyl group, C I ⁇ C 2 Al Kirucheniru group, a pyridyl group, C ⁇ C i Two alkylpyridyl groups are preferred.
  • the terminal group of the crude polymer fluorescent substance may be protected with a stable group, since if the polymerization active group remains as it is, the light-emitting characteristics and life of the element may be reduced.
  • Those having a conjugate bond continuous with the conjugate structure of the main chain are preferable, and examples thereof include a structure bonded to an aryl group or a heterocyclic compound group via a vinylene group. Specific examples thereof include the substituents described in Chemical Formula 10 of JP-A-9-145478.
  • the polymeric fluorescent substance obtained by the production method of the present invention also has substantially the same repeating units as the crude polymeric fluorescent substance used in the production.
  • a method for synthesizing the crude polymer fluorescent substance when a main chain has a vinylene group, for example, a method described in Japanese Patent Application Laid-Open No. H5-220355 may be mentioned. That is, polymerization of a dialdehyde compound and a diphosphonium salt compound by a Wittig reaction, polymerization of a divinyl compound and a dihalogen compound or Heck reaction of a vinylamine compound alone, and polymerization of a dialdehyde compound and a diphosphorous acid.
  • a method of polymerizing the corresponding monomer by a Suzuki coupling reaction for example, a method of polymerizing by a Grignard reaction, a method of polymerizing by a Ni (0) catalyst, Fe method of polymerizing Ri by the oxidizing agent, such as C l 3, electrochemically methods oxidative polymerization, a method by decomposition of an intermediate polymer that have a suitable leaving group can be exemplified.
  • the polymer fluorescent substance of the present invention When the polymer fluorescent substance of the present invention is used as a light emitting material for a polymer LED, its purity affects the emission characteristics. Therefore, the monomer before polymerization of the crude polymer fluorescent substance is distilled, sublimated, purified and recrystallized. It is preferable to polymerize after purifying by such a method.
  • the crude polymer fluorescent material has a formula within a range that does not impair the fluorescence characteristics and the charge transport characteristics.
  • a repeating unit other than the repeating unit represented by (1) may be included. Further, the repeating unit represented by the formula (1) and other repeating units may be connected by a non-conjugated portion, or the repeating unit may include the non-conjugated portion.
  • Examples of the bonding structure containing the non-conjugated moiety include the following, a combination of the following and a vinylene group, and a combination of two or more of the following.
  • R is a group selected from the same substituents as described above, and Ar represents a hydrocarbon group having 6 to 60 carbon atoms.
  • the crude polymer fluorescent substance may be a random, block or graft copolymer, or a polymer having an intermediate structure between them, for example, a random copolymer having a block property.
  • a random copolymer-block or graft copolymer having a block property is preferable to a complete random copolymer. If the main chain is branched and has three or more terminal groups, ⁇ dendrimers are also included.
  • a crude polymer fluorescent material having fluorescence in a solid state is preferably used.
  • good solvents for the crude polymer fluorescent substance include chloroform form, methylene chloride, dichloroethane, tetrahydrofuran, toluene, xylene, mesitylene, decalin, n-butylbenzene, dioxane and the like. Although it depends on the structure and molecular weight of the polymeric fluorescent substance, usually, it is possible to dissolve it in these solvents in an amount of 0.1% by weight or more.
  • the structure of the polymer LED of the present invention has a light emitting layer between a pair of anodes and cathodes, at least one of which is transparent or translucent.
  • a molecular phosphor is included in the light emitting layer.
  • the polymer LED of the present invention includes a polymer LED having an electron transport layer between a cathode and a light-emitting layer, a polymer LED having a hole transport layer between an anode and a light-emitting layer, and a cathode.
  • Polymer LED in which an electron transporting layer is provided between the light emitting layer and the anode, and a hole transporting layer is provided between the anode and the light emitting layer.
  • the light emitting layer is a layer having a function of emitting light
  • the hole transport layer is A layer having a function of transporting electrons.
  • An electron transporting layer has a function of transporting electrons.
  • Layer Note that the electron transport layer and the hole transport layer are collectively called a charge transport layer. Two or more light emitting layers, hole transport layers, and electron transport layers may be used independently.
  • the charge transport layers provided adjacent to the electrodes those having the function of improving the charge injection efficiency from the electrodes and having the effect of lowering the driving voltage of the device are particularly suitable for the charge injection layer (hole injection layer).
  • the above-described charge injection layer or an insulating layer having a thickness of 2 nm or less may be provided adjacent to the electrode in order to improve adhesion to the electrode and improve charge injection from the electrode.
  • a thin buffer layer may be inserted at the interface between the charge transport layer and the light-emitting layer for the purpose of improvement and prevention of mixing.
  • the order and number of layers to be stacked and the thickness of each layer can be appropriately used in consideration of luminous efficiency and device life.
  • the polymer LED provided with a charge injection layer includes a polymer LED provided with a charge injection layer adjacent to a cathode, and a charge injection layer adjacent to an anode.
  • Polymer LED provided.
  • the charge injection layer include a layer containing a conductive polymer, an anode and a hole transport layer. Between the anode material and the hole transport material contained in the hole transport layer. A layer containing a material having an ionization potential of, and a layer provided between the cathode and the electron transport layer and containing a material having an electron affinity of an intermediate value between the P pole material and the electron transport material contained in the electron transport layer And the like.
  • the conductive polymer When the charge injection layer is a layer containing a conductive polymer, the conductive polymer preferably has an electric conductivity of 10 to 5 SZcm or more and 10 3 S / cm or less. 10 0 to make it smaller. S / cm or more 10 2 SZcm hereinafter more preferably, 10- 5 SZcm or more and 10 1 S / cm or less is more preferred. Normally in order to electrically conductivity 10- 5 S / cm or more 10 3 S / cm or less under the conducting polymer, a suitable amount of ions are doped into the conducting polymer.
  • the kind of ions to be doped is an anion for the hole injection layer and a cation for the electron injection layer.
  • anions include polystyrenesulfonate, alkylbenzenesulfonate, camphorsulfonate, and the like.
  • cations include lithium, sodium, potassium, and tetrabutylammonium. And the like.
  • the thickness of the charge injection layer is, for example, 1 nm to 100 nm, and preferably 2 nm to 50 nm.
  • the material used for the charge injection layer may be appropriately selected in relation to the material of the electrode and the adjacent layer.
  • the insulating layer having a thickness of 2 nm or less has a function of facilitating charge injection.
  • Examples of the material for the insulating layer include metal fluorides, metal oxides, and organic insulating materials.
  • S Polymer LEDs with an insulation layer of 2 nm or less in thickness include polymer LEDs with an insulation layer of 2 nm or less adjacent to the cathode, and insulation of 2 nm or less adjacent to the anode. A polymer LED having a layer is exemplified.
  • the optimum value of the thickness of the light emitting layer differs depending on the material used, and may be selected so that the driving voltage and the light emitting efficiency have appropriate values.
  • the thickness is 1 nm to 1 ⁇ m, and preferably 2 ⁇ ⁇ ! 5500 nm, more preferably 5 nm n200 nm.
  • a light-emitting material other than the above-described polymer fluorescent substance obtained by the production method of the present invention may be mixed and used in the light-emitting layer.
  • the invention of the present application In the molecular LED, a light emitting layer containing a light emitting material other than the polymer fluorescent substance may be laminated with the light emitting layer containing the polymer fluorescent substance.
  • the light emitting material known materials can be used.
  • low molecular compounds include naphthalene derivatives, anthracene or derivatives thereof, perylene or derivatives thereof, polymethine-based, xanthene-based, coumarin-based, and cyanine-based dyes, metal complexes of 8-hydroxyquinoline or derivatives thereof, and aromatics.
  • amine, tetraphenylcyclopentadiene or a derivative thereof, or tetraphenylbutadiene or a derivative thereof can be used.
  • JP-A-57-51781 and JP-A-59-194393 can be used.
  • the hole transport material used includes polyvinyl carbazole or a derivative thereof, polysilane or a derivative thereof, and an aromatic amine in a side chain or a main chain.
  • JP-A-63-70257, JP-A-63-175860, JP-A-2-135359, JP-A-2-135361, JP-A-209988 examples thereof include those described in JP-A-3-37992 and JP-A-3-152184.
  • a hole transporting material used for the hole transporting layer polyvinyl carbazole or a derivative thereof, polysilane or a derivative thereof, a polysiloxane derivative having an aromatic amine compound group in a side chain or a main chain, or a polyaniline.
  • a high molecular weight hole transporting material such as phosphorus or a derivative thereof, polythiophene or a derivative thereof, poly (p-phenylenevinylene) or a derivative thereof, or poly (2,5-chenylenevinylene) or a derivative thereof is preferable. More preferably, polybulcarpazole or its derivative, polysilane or its derivative, side chain or main chain A polysiloxane derivative having an aromatic amine in the chain. In the case of a low molecular weight hole transporting material, it is preferable to use it by dispersing it in a high molecular binder.
  • Polyvinylcarbazole or a derivative thereof can be obtained, for example, from a Bier monomer by force polymerization or radical polymerization.
  • siloxane skeleton structure has little hole-transport property
  • those having the structure of the above-described low-molecular-weight hole-transport material in a side chain or a main chain are preferably used as the polysiloxane or a derivative thereof.
  • those having an aromatic amine having a hole transporting property in a side chain or a main chain are exemplified.
  • the method of forming the hole transport layer There is no limitation on the method of forming the hole transport layer.
  • a method of forming a film from a mixed solution with a polymer binder is exemplified.
  • a method of forming a film from a solution is exemplified.
  • the solvent used for film formation from a solution is not particularly limited as long as it dissolves the hole transport material.
  • the solvent include chlorinated solvents such as chloroform, methylene chloride and dichloroethane, ether solvents such as tetrahydrofuran, aromatic hydrocarbon solvents such as toluene and xylene, and ketones such as acetone and methyl ethyl ketone.
  • the solvent include ester solvents such as ethyl acetate, butyl acetate and ethyl cellosolve acetate.
  • Solution coating methods include spin coating, casting, microgravure coating, gravure coating, percoating, roll coating, wire bar coating, dip coating, spray coating, and screen coating from solution.
  • Coating methods such as a printing method, a flexographic printing method, an offset printing method, and an ink jet printing method can be used.
  • polymer binder to be mixed those which do not extremely inhibit charge transport are preferable, and those which do not strongly absorb visible light are preferably used.
  • the polymer binder include polycarbonate, polyatarylate, and polymethyl atalay. , Polymethyl methacrylate, polystyrene, polyvinyl chloride, polysiloxane, and the like.
  • the optimal value of the thickness of the hole transport layer depends on the material used, and may be selected so that the driving voltage and the luminous efficiency are at appropriate values, but at least a thickness that does not cause pinholes is necessary. If the thickness is too large, the driving voltage of the device becomes high, which is not preferable. Therefore, the thickness of the hole transport layer is, for example, 1 nm to 1 im, preferably 2 nm to 500 nm, and more preferably 5 nm to 200 nm.
  • any known electron transporting material can be used, such as oxadiazole derivative, anthraquinodimethane or its derivative, benzoquinone or its derivative, naphthoquinone or its derivative.
  • Derivative, anthraquinone or its derivative, tetracyanoanthraquinodimethane or its derivative, fluorenone derivative, diphenyldicyanoethylene or its derivative, diphenoquinone derivative, or metal complex of 8-hydroxyquinoline or its derivative, polyquinoline or Derivatives thereof, polyquinoxaline or a derivative thereof, polyfluorene or a derivative thereof and the like are exemplified.
  • oxadiazole derivatives benzoquinone or its derivatives, anthraquinone or its derivatives, or metal complexes of 8-hydroxyquinoline or its derivatives, polyquinoline or its derivatives, polyquinoxaline or its derivatives, and polyfluorene or its derivatives are preferred.
  • 2- (4-biphenylyl) -5- (4-t-butylphenyl) 1,1,3,4-oxadiazole, benzoquinone, anthraquinone, tris (8-quinolino-mono) aluminum, and polyquinoline are more preferred.
  • the film formation method of the electron transport layer There is no particular limitation on the film formation method of the electron transport layer.
  • a vacuum deposition method from powder or a film formation method from a solution or a molten state is used.
  • the electron transport material a method by film formation from a solution or a molten state is exemplified.
  • a polymer binder may be used in combination.
  • the solvent used for film formation from a solution is not particularly limited as long as it can dissolve the electron transport material and / or the polymer binder.
  • the solvent examples include chlorinated solvents such as chlorophonolem, dimethyl chloride and dichloroethane, ether solvents such as tetrahydrofuran, aromatic hydrocarbon solvents such as toluene and xylene, ketone solvents such as acetone and methyl ethyl ketone, ethyl acetate, and acetic acid.
  • chlorinated solvents such as chlorophonolem, dimethyl chloride and dichloroethane
  • ether solvents such as tetrahydrofuran
  • aromatic hydrocarbon solvents such as toluene and xylene
  • ketone solvents such as acetone and methyl ethyl ketone
  • ethyl acetate examples of the solvent
  • Ester solvents such as butyl and ethyl cellosolve acetate are exemplified.
  • An application method such as an ink-jet printing method, a flexographic printing method, an offset printing method, and an ink-jet printing method can be used.
  • polymer binder to be mixed, those which do not extremely inhibit charge transport are preferable, and those which do not strongly absorb visible light are preferably used.
  • Poly ( ⁇ ⁇ ⁇ -vinylcarbazole) is used as the polymer binder.
  • the thickness of the electron transporting layer depends on the material used, and may be selected so that the driving voltage and the luminous efficiency are appropriate. However, at least a thickness that does not cause pinholes is necessary. Yes, too thick is not desirable because the driving voltage of the device is high. Therefore, the thickness of the electron transport layer is, for example, 1 nm to 1 im, preferably 2 nm to 500 nm, and more preferably 5 ⁇ ! ⁇ 200 nm.
  • the substrate on which the polymer LED of the present invention is formed may be any substrate as long as it does not change when an electrode is formed and an organic layer is formed.
  • the substrate on which the polymer LED of the present invention is formed may be any substrate as long as it does not change when an electrode is formed and an organic layer is formed.
  • glass, plastic, polymer And a silicon substrate In the case of an opaque substrate, the opposite electrode is preferably transparent or translucent.
  • the anode side is preferably transparent or translucent.
  • a conductive metal oxide film, a translucent metal thin film, or the like is used as the material of the anode. Specifically, it is made using conductive glass consisting of indium oxide, zinc oxide, tin oxide, and their composites, such as indium tin oxide (ITO), aluminum oxide, oxide, and oxide. Films (eg, NESA), gold, platinum, silver, copper, etc., are used, and ITO, indium oxide, zinc oxide, and tin oxide are preferred. Examples of the manufacturing method include a vacuum evaporation method, a sputtering method, an ion plating method, and a plating method.
  • An organic transparent conductive film such as polyaniline or a derivative thereof, polythiophene or a derivative thereof may be used as the anode.
  • the thickness of the anode can be appropriately selected in consideration of light transmittance and electric conductivity, and is, for example, from 10 nm to 10 ⁇ , preferably from 20 nm to 1 ⁇ m. And more preferably 50 nm to 500 nm.
  • a layer made of a phthalocyanine derivative, a conductive polymer, carbon, or the like, or an average film thickness made of a metal oxide, a metal fluoride, an organic insulating material, or the like is formed on the anode. Even if a layer of nm or less is provided.
  • a material having a small work function is preferable.
  • metals such as lithium, sodium, potassium, norebium, cesium, beryllium, magnesium, calcium, strontium, barium, anorenium, scandium, vanadium, zinc, yttrium, indium, cerium, samarium, europium, terbium, ytterbium, etc. ⁇ Alloys of two or more of them, or one or more of them, and one or more of gold, silver, platinum, copper, manganese, titanium, copanoleto, nickele, tungsten, and tin, graphs Aite or a graphite interlayer compound is used.
  • the cathode may have a laminated structure of two or more layers.
  • the thickness of the cathode can be appropriately selected in consideration of electric conductivity and durability, for example, 10 11 111 to 10 ⁇ , preferably 2 O nm to l / im, More preferably, it is 50 nm to 500 nm.
  • a vacuum evaporation method, a sputtering method, a lamination method of thermocompression bonding of a metal thin film, and the like are used as a method for producing the cathode.
  • a layer made of a conductive polymer or a layer made of a metal oxide, a metal fluoride, an organic insulating material, or the like having an average thickness of 2 nm or less may be provided between the cathode and the organic material layer.
  • a protective layer for protecting the polymer LED may be attached. In order to use the polymer LED stably for a long period of time, it is preferable to attach a protective layer and Z or a protective cover to protect the element from the outside.
  • a polymer compound, a metal oxide, a metal fluoride, a metal boride and the like can be used.
  • a glass plate, a plastic plate whose surface has been subjected to a low water permeability treatment, or the like can be used, and the cover is bonded to the element substrate with a heat effect resin or a photocurable resin to seal the cover. Is preferably used. If the space is maintained using a spacer, it is easy to prevent the element from being damaged. By enclosing an inert gas such as nitrogen or argon in the space, it is possible to prevent oxidation of the cathode, and by installing a desiccant such as an oxidation slurry in the space. It becomes easy to suppress the moisture adsorbed in the manufacturing process from damaging the element. It is preferable to take one or more of these measures.
  • a planar anode and a planar cathode may be arranged so as to overlap.
  • a method in which a mask having a patterned window provided on the surface of the planar light emitting element is provided.
  • There is a method of emitting light a method of forming one or both of an anode and a cathode in a pattern.
  • both the anode and the cathode may be formed in a stripe shape and arranged so as to be orthogonal to each other.
  • a method of applying different types of polymer phosphors with different emission colors, a color filter Depending on the method using one or a fluorescence conversion filter, partial color display and multi-color display can be realized.
  • the dot matrix element can be driven passively or may be driven actively in combination with a TFT or the like.
  • These display elements can be used as display devices for computers, televisions, mobile terminals, mobile phones, car navigation systems, video camera viewfinders, and the like.
  • planar light emitting element is a self-luminous thin type, and can be suitably used as a planar light source for packing in a liquid crystal display device or a planar illumination light source. Also, if a flexible substrate is used, it can be used as a curved light source or display device.
  • the number average molecular weight was determined by gel permeation chromatography (GPC) using the form of solvent as a solvent, and the number average molecular weight in terms of polystyrene was determined.
  • this polymer is dissolved in tetrahydrofuran, and this is poured into methanol. And purified by reprecipitation. After washing the precipitate with methanol, 50. It was dried under reduced pressure at C for 8 hours to obtain 4.41 g of a polymer.
  • the mixture was cooled to 50 ° C. and neutralized by adding a mixed solution of 1.1 g / l of acetic acid and 1.1 g of 4-dioxane. After allowing to cool to room temperature, the reaction solution was poured into stirred ion-exchanged water. Next, the deposited precipitate was separated by filtration and washed with methanol. This was dried under reduced pressure at 50 ° C for 4 hours to obtain 0.888 g of a polymer.
  • polymeric fluorescent substance 1 This was dissolved in tetrahydrofuran, poured into methanol, and purified by reprecipitation. The precipitate was washed with methanol and dried under reduced pressure at 50 ° C for 5.5 hours to obtain 85 g of a polymer. This polymer is referred to as polymeric fluorescent substance 1.
  • the 0.4% toluene solution of polymeric fluorescent substance 1 became a homogeneous solution when heated, and did not become entrapped even at room temperature.
  • polymer fluorescent substance 2 the crude polymer fluorescent substance before the initial processing is referred to as polymer fluorescent substance 2.
  • the number average molecular weight in terms of polystyrene of the polymeric fluorescent substance 2 is 4.3 X 1
  • a glass substrate on which an IT ⁇ film with a thickness of 150 nm was applied by sputtering was spin-coated with a solution of poly (ethylenedioxythiophene) / polystyrene sulfonic acid (Baytron, Baytron) by spin coating. Deposited to a thickness of nm and 120 on a hot plate. Dry at C for 5 minutes. Next, a film having a thickness of 100 nm was formed by spin coating using a polymer solution of 0.4 wt% of a polymeric fluorescent substance 1 in a pore form.
  • 9,9-dioctylfluorene-1,2,7-bis (ethylenpolonate) (900 mg, 1.641 mmo 1)
  • 2,7-dibromo-1,9,9-dioctylfluorene 914 mg, 1.723 mm o 1)
  • a 1 iquat 336 66 O mg
  • tetrakis (triphenylphosphine) palladium (57 mg, 0.0492 mmo 1) was added, and the mixture was heated under reflux for 20 hours. After allowing to cool, liquid separation was performed, and the organic layer was washed with water. The organic layer was dropped into methanol (300 ml), and the deposited precipitate was separated by filtration. The polymer was purified by silica gel chromatography (toluene) to obtain a polymer. The yield was 863 mg. The polystyrene-equivalent number average molecular weight of the polymer was 1.3 ⁇ 10 4 .
  • polymeric fluorescent substance 3 was soluble in solvents such as toluene and black-mouthed form.
  • a 0.4% chloroform solution of polymeric fluorescent substance 3 was spin-coated on a quartz plate to form a thin film of polymeric fluorescent substance 3.
  • the ultraviolet-visible absorption spectrum and the fluorescence spectrum of this thin film were measured using an ultraviolet-visible absorption spectrophotometer (Hitachi Ltd. UV3500) and a fluorescence spectrophotometer (Hitachi Ltd. 850), respectively.
  • the fluorescence spectrum when excited at 350 nm was used to calculate the fluorescence intensity.
  • the relative value of the fluorescence intensity was obtained by dividing the area of the fluorescence spectrum plotted with the wave number on the horizontal axis by the absorbance at 350 nm.
  • the fluorescent peak wavelength of polymeric fluorescent substance 3 was 428 ⁇ , and the relative value of the fluorescent intensity was 3.1.
  • the crude polymer fluorescent material before the initial processing is referred to as a polymer fluorescent material 4.
  • a polymeric fluorescent substance 4 the UV-visible absorption peak and the fluorescent spectrum were measured in the same manner as in Example 3, and the relative value of the fluorescent intensity was obtained.
  • the fluorescent peak wavelength of polymeric fluorescent substance 4 was 426 nm, and the relative value of the fluorescent intensity was 0.26.
  • the polymeric fluorescent substance obtained by the production method of the present invention has excellent solubility in an organic solvent and can be suitably used as a polymeric LED or a dye for laser.
  • the polymer LED using the polymer phosphor obtained by the manufacturing method has low voltage and high luminous efficiency. Therefore, the polymer LED has a curved or planar light source as a backlight, a segment type display element, and a dot matrix flat panel.
  • 'It can be used preferably for devices such as Ray.

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  • Medicinal Chemistry (AREA)
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Abstract

L'invention concerne un procédé de production d'un matériau fluorescent polymérique placé au contact d'un alcali, qui se caractérise en ce qu'il comprend une étape dans laquelle un matériau fluorescent polymérique brut émettant une fluorescence à l'état solide présente un poids moléculaire moyen en nombre compris entre 10?4 et 108¿ pour ce qui est du polystyrène, et comprend un ou deux types d'unités récurrentes de la formule (1) dans laquelle Ar¿1? représente un groupe arylène ou d'un composé hétérocyclique comprenant éventuellement un ou plusieurs substituants; R1 et R2 représentent chacun, indépendamment, hydrogène ou un groupe sélectionné dans le groupe constitué par des groupes alkyle, aryle, d'un composé hétérocyclique, et cyano, à condition que les groupes aryle et du composé hétérocyclique soient éventuellement substitués; et n est 0 ou 1.
PCT/JP2001/005219 1999-12-20 2001-06-19 Materiau fluorescent polymerique, procede de production, et element luminescent polymerique WO2002102925A1 (fr)

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JP2000384951A JP4940493B2 (ja) 1999-12-20 2000-12-19 高分子蛍光体、その製造方法および高分子発光素子
US10/480,996 US7357990B2 (en) 1999-12-20 2001-06-19 Polymeric fluorescent material, process for producing the same, and polymeric luminiscent element
PCT/JP2001/005219 WO2002102925A1 (fr) 1999-12-20 2001-06-19 Materiau fluorescent polymerique, procede de production, et element luminescent polymerique
DE10197249T DE10197249T5 (de) 1999-12-20 2001-06-19 Polymere fluoreszierende Substanz, Herstellungsverfahren dafür und polymere Licht emittierende Vorrichtung

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JP2000384951A JP4940493B2 (ja) 1999-12-20 2000-12-19 高分子蛍光体、その製造方法および高分子発光素子
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JP4482994B2 (ja) * 1999-12-27 2010-06-16 住友化学株式会社 高分子蛍光体の製造方法および高分子発光素子
SG125077A1 (en) 2001-12-19 2006-09-29 Sumitomo Chemical Co Copolymer, polymer composition and polymer light-emitting device
WO2004009669A1 (fr) * 2002-07-18 2004-01-29 Toyo Gosei Co., Ltd. Procede de production d'un dendrimere, formation d'un compose bloc et procede de produciton d'un compose thiophene
US20070103059A1 (en) * 2003-05-16 2007-05-10 Sumitomo Chemical Company, Limited Composition and polymer light-emitting device
DE112004001661T5 (de) * 2003-09-12 2006-07-06 Sumitomo Chemical Co., Ltd. Lichtemittierendes Material und lichtemittierende Vorrichtung unter Verwendung desselben
TW200619300A (en) * 2004-08-31 2006-06-16 Sumitomo Chemical Co Luminescent-polymer composition and luminescent -polymer device
DE112006002642T5 (de) 2005-10-07 2008-08-21 Sumitomo Chemical Company, Ltd. Polymer und polymeres lumineszierendes Element, welches dieses verwendet
JP2008056911A (ja) * 2006-07-31 2008-03-13 Sumitomo Chemical Co Ltd 高分子化合物の製造方法
WO2008016090A1 (fr) * 2006-07-31 2008-02-07 Sumitomo Chemical Company, Limited Procédé de production d'un composé polymère
KR20090034392A (ko) * 2006-07-31 2009-04-07 스미또모 가가꾸 가부시키가이샤 고분자 화합물 및 그것을 이용한 고분자 발광 소자
WO2008140057A1 (fr) * 2007-05-11 2008-11-20 Sumitomo Chemical Company, Limited Compose polymere et son procede de production, et materiau emettant de la lumiere, composition liquide, film mince, dispositif polymere emettant de la lumiere, source lumineuse de surface, dispositif d'affichage, transistor organique et cellule solaire, chacun utilisant le compose
WO2008140056A1 (fr) * 2007-05-11 2008-11-20 Sumitomo Chemical Company, Limited Composé polymere et son procede de production, et materiau emettant de la lumiere, composition liquide, film mince, dispositif polymere emettant de la lumiere, source lumineuse de surface, dispositif d'affichage, transistor organique et cellule solaire, chacun utilisant le compose
EP2159243A4 (fr) * 2007-05-23 2011-11-09 Sumitomo Chemical Co Composé polymère et son procédé de production, matériau électroluminescent, composition liquide, couche mince, dispositif électroluminescent polymère, source lumineuse de surface, dispositif d'affichage, transistor organique et cellule solaire, chacun l'utilisant

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