US20050255391A1 - Polymerisable diketopyrrolopyrroles, use of such compounds in colour filters and polymers prepared from these compounds - Google Patents

Polymerisable diketopyrrolopyrroles, use of such compounds in colour filters and polymers prepared from these compounds Download PDF

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US20050255391A1
US20050255391A1 US10/522,212 US52221205A US2005255391A1 US 20050255391 A1 US20050255391 A1 US 20050255391A1 US 52221205 A US52221205 A US 52221205A US 2005255391 A1 US2005255391 A1 US 2005255391A1
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alkyl
independently
hydrogen
formula
group
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Jean-Marie Adam
Gerardus de Keyzer
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BASF Corp
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Assigned to CIBA SPECIALTY CHEMICAL CORP. reassignment CIBA SPECIALTY CHEMICAL CORP. ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: ADAM, JEAN-MARIE, DE KEYZER, GERARDUS
Publication of US20050255391A1 publication Critical patent/US20050255391A1/en
Priority to US12/006,520 priority Critical patent/US7723530B2/en
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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
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B69/00—Dyes not provided for by a single group of this subclass
    • C09B69/10—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds
    • C09B69/109—Polymeric dyes; Reaction products of dyes with monomers or with macromolecular compounds containing other specific dyes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09B—ORGANIC DYES OR CLOSELY-RELATED COMPOUNDS FOR PRODUCING DYES, e.g. PIGMENTS; MORDANTS; LAKES
    • C09B57/00—Other synthetic dyes of known constitution
    • C09B57/004—Diketopyrrolopyrrole dyes
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B5/00—Optical elements other than lenses
    • G02B5/20—Filters
    • G02B5/22—Absorbing filters
    • G02B5/223—Absorbing filters containing organic substances, e.g. dyes, inks or pigments
    • G—PHYSICS
    • G02—OPTICS
    • G02F—OPTICAL DEVICES OR ARRANGEMENTS FOR THE CONTROL OF LIGHT BY MODIFICATION OF THE OPTICAL PROPERTIES OF THE MEDIA OF THE ELEMENTS INVOLVED THEREIN; NON-LINEAR OPTICS; FREQUENCY-CHANGING OF LIGHT; OPTICAL LOGIC ELEMENTS; OPTICAL ANALOGUE/DIGITAL CONVERTERS
    • G02F1/00—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics
    • G02F1/01—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour 
    • G02F1/13—Devices or arrangements for the control of the intensity, colour, phase, polarisation or direction of light arriving from an independent light source, e.g. switching, gating or modulating; Non-linear optics for the control of the intensity, phase, polarisation or colour  based on liquid crystals, e.g. single liquid crystal display cells
    • G02F1/133—Constructional arrangements; Operation of liquid crystal cells; Circuit arrangements
    • G02F1/1333—Constructional arrangements; Manufacturing methods
    • G02F1/1335—Structural association of cells with optical devices, e.g. polarisers or reflectors
    • G02F1/133509—Filters, e.g. light shielding masks
    • G02F1/133514—Colour filters

Definitions

  • the present invention relates to the use of polymerisable diketopyrrolopyrroles in colour filters, which can themselves be used for example in electro-optical systems such as TV screens, liquid crystal displays, charge coupled devices, plasma displays or electroluminescent displays and the like. These may be, for example, active (twisted nematic) or passive (supertwisted nematic) ferroelectric displays or light-emitting diodes.
  • the present invention relates to colour filters comprising a transparent substrate and a layer comprising from 1 to 75% by weight, preferably from 5 to 50% by weight, with particular preference from 25 to 40% by weight, based on the overall weight of the layer, of a diketopyrrolopyrrole of the general formula (I) dispersed in a high molecular mass organic material: wherein A and B independently of one another are a group of the formula
  • X 1 is preferably a single bond, —O—, —S—, —NH—, —CONH—, or —SO 2 —NH—.
  • X 2 is preferably an alkylene spacer containing optionally one or more, in particular one or two groups, —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— as linking bridge.
  • the number of carbon atoms of the alkylene spacer is preferably greater than 4, more preferred greater than 6 and most preferred in the range of 8 to 16.
  • X 3 is preferably —OH, —NH 2 , —OC(O)—C(R 12 ) ⁇ CH 2 , —C(O)—C(R 12 ) ⁇ CH 2 , or —OC(O)—N—X 4 —N—C(O)—O—X 5 —O—C(O)—C(R 12 ) ⁇ CH 2 ; wherein R 12 is hydrogen, or methyl, and X 4 and X 5 are as defined above.
  • the diketopyrrolopyrroles have the general formula wherein R 1 and R 2 are independently of each other a group of the formula —X 2 —X 3 (II), wherein
  • diketopyrrolopyrroles of formula I do not tend to aggregate and, hence, show very good dispersibility.
  • Color filters prepared by using the diketopyrrolopyrroles of formula I have high transparence and pure hue. In addition, they facilitate adjustment of color points and enable a large choice of shades.
  • the pigments will generally be used in the manufacture of colour filters as a dispersion in an organic solvent or water. There are several ways to manufacture these colour filters, which follow two mainstreams:
  • Direct patterning can be obtained by several printing techniques, such as impact (off-set, flexography, stamping, letterpress etc.) as well as non-impact (ink jet techniques).
  • impact off-set, flexography, stamping, letterpress etc.
  • non-impact ink jet techniques
  • the pigment may be dispersed in water or organic solvents by standard de-agglomeration methods (Skandex, Dynomill, Dispermat and the like) in the presence of a dispersant and a polymeric binder to produce an ink.
  • Any dispersion technique known in the field including the choice of solvent, dispersant and binder, can be used.
  • the type of ink and its viscosity depend on the application technique and are well-known to the skilled artisan.
  • Most usual binders, to which the invention is of course not limited, are (meth)acrylates, epoxies, PVA, polyimids, Novolak systems and the like as well as combinations of these polymers.
  • the ink dispersion then can be printed on all kind of standard printing machines. Curing of the binder system is preferably achieved by a heating process.
  • the three colours can be applied at once or in different printing steps with intermediate drying and/or curing steps, for example one colour at the time in three printing steps.
  • Inks for use in ink jet can be prepared likewise. They generally contain a pigment dispersed in water and/or one or a mixture of many hydrophilic organic solvents in combination with a dispersant and a binder.
  • a standard ink jet printer can be used or a dedicated printer can be built in order to optimize for example the printing speed etc.
  • a web system For lamination techniques, like thermal transfer and the like, a web system has to be made:
  • the pigment is dispersed in a solvent or water with dispersant and binder and coated on a foil and dried.
  • the pigment/binder system can be patternwise or uniformly transferred to a colour filter substrate with the help of energy (UV, IR, heat, pressure etc.).
  • the colourant for example may be transferred alone (dye diffusion or sublimation transfer), or the colourant dispersion may be entirely transferred including the binder (wax transfer).
  • the pigment has to be dispersed in water together with an ionized polymer.
  • the ionized polymer is deionized at the anode or the cathode and, being insoluble then, deposited together with the pigments. This can be done on patterned or patternwise shielded, by a photoresist, (transparent) photo-conductors like ITO etc.
  • the ChromalinTM process makes use of a photosensitive material, deposited on a colour filter substrate.
  • the material becomes tacky upon UV exposure.
  • the so called ‘toner’ comprising a mixture or compound of pigment and polymer, is distributed on the substrate and sticks on the tacky parts. This process has to be done three to four times for R, G, B and eventually black.
  • Patterning after applying is a method based mostly on the known photoresist technology, wherein the pigment is dispersed in the photoresist composition. Other methods are indirect patterning with the help of a separate photoresist or lamination techniques.
  • the pigment may be dispersed into photoresists by any standard method such as described above for the printing processes.
  • the binder systems may also be identical. Further suitable compositions are described for example in EP 654711, WO 98/45756 or WO 98/45757.
  • Photoresists comprise a photoinitiator and a poly-crosslinkable monomer (negative radical polymerization), a material to crosslink the polymers itself (for example a photoacid generator or the like) or a material to chemically change the solubility of the polymer in certain developing media.
  • This process can also be done with heat (for example using thermal arrays or an NIR beam) instead of UV, in the case of some polymers which undergo chemical changes during heating processes, resulting in changes of solubility in the mentioned developing media.
  • a photoinitiator is then not needed.
  • the photosensitive or heat sensible material is coated on a colour filter substrate, dried and UV(or heat) irradiated, sometimes again baked (photoacid generators) and developed with a developing medium (mostly a base). In this last step only the non-exposed (negative systems) or only the exposed (positive systems) parts are washed away, giving the wanted pattern. This operation has to be repeated for all the colours used.
  • Photosensitive lamination techniques are using the same principle, the only difference being the coating technique.
  • a photosensitive system is applied as described above, however on a web instead of a colour filter substrate.
  • the foil is placed on the colour filter substrate and the photosensitive layer is transferred with the help of heat and/or pressure.
  • substantially colourless methacrylic resins are commonly used in colour filters, examples thereof which are known to the skilled artisan being copolymers of aromatic methacrylates with methacrylic acid of Mw from 30,000 to 60,000. Such resins are highly appropriated to make films by spin-coating.
  • the colour filters of the invention contain the pigment compositions of the invention judiciously in a concentration of from 1 to 75% by weight, preferably from 5 to 50% by weight, with particular preference from 25 to 40% by weight, based on the overall weight of the pigmented layer.
  • the invention therefore likewise provides a colour filter comprising a transparent substrate and a layer comprising from 1 to 75% by weight, preferably from 5 to 50% by weight, with particular preference from 25 to 40% by weight, based on the overall weight of the layer, of a pigment composition of the invention or the individual components of said composition dispersed in a high molecular mass organic material.
  • the substrate is preferably essentially colourless (T ⁇ 95% all over the visible range from 400 to 700 nm).
  • the instant printing inks or photoresists for making colour filters contain the pigment compositions of the invention judiciously in a concentration of from 0.01 to 40% by weight, preferably from 1 to 25% by weight, with particular preference from 5 to 10% by weight, based on the overall weight of the printing ink or photoresist.
  • the invention therefore likewise provides a composition for making colour filters comprising from 0.01 to 40% by weight, preferably from 1 to 25% by weight, with particular preference from 5 to 10% by weight, based on the overall weight of the composition, of a pigment composition of the invention dispersed therein.
  • This pigment composition also may additionally contain other colorants of different structure.
  • the additional components will shift the mixture's spectrum hypsochromically or batho-chromically depending on their own hue.
  • colorants can additionally be used, and in which amounts, depending on the desired colour.
  • it is advantageous to use the inventive compositions in mixture or in combination with other additives such as wetting agents, surfactants, defoamers, antioxidants, UV absorbers, light stabilizers, plastisizers, or general texture improving agents and so forth.
  • additives can be used in a concentration from about 0.1 to 25 percent, preferably from about 0.2 to 15% and most preferably from about 0.5 to 8%, by weight based on the total weight of (a), (b) and (c).
  • Suitable surfactants include anionic surfactants such as alkylbenzene- or alkylnaphthalene-sulfonates, alkylsulfosuccinates or naphthalene formaldehyde sulfonates; cationic surfactants including, for example, quaternary salts such as benzyl tributyl ammonium chloride; or nonionic or amphoteric surfactants such as polyoxyethylene surfactants and alkyl- or amidopropyl betaines, respectively.
  • anionic surfactants such as alkylbenzene- or alkylnaphthalene-sulfonates, alkylsulfosuccinates or naphthalene formaldehyde sulfonates
  • cationic surfactants including, for example, quaternary salts such as benzyl tributyl ammonium chloride
  • nonionic or amphoteric surfactants such as polyoxyethylene surfactants
  • Suitable texture improving agents are, for example, fatty acids such as stearic acid or behenic acid, and fatty amines such as laurylamine and stearylamine.
  • fatty alcohols or ethoxylated fatty alcohols, polyols such as aliphatic 1,2-diols or epoxidized soy bean oil, waxes, resin acids and resin acid salts may be used for this purpose.
  • Suitable UV stabilizers are, for example, the known benzotriazole derivatives (see, for example, U.S. Pat. No. B1-6,184,375, column 20, line 48 to column 21, line 15) and 2-(2-hydroxyphenyl)-1,3,5-triazines (see, for example, U.S. Pat. No. B1-6,184,375, column 22, line 41 to 65) known under the trade name TINUVIN® or CIBA® Fast H Liquid an aryl sulfonated benzotriazol, both being products of CIBA Specialty Chemicals Corporation.
  • halogen is generally iodine, fluorine, bromine or chlorine, preferably bromine or chlorine.
  • C 1 -C 4 alkyl group is methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl or tert-butyl;
  • C 1 -C 8 alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-amyl, tert-amyl or hexyl;
  • C 1 -C 18 alkyl is, for example, methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert-butyl, n-amyl, tert-amyl, hexyl, heptyl, octyl, 2-ethylhexyl, nonyl, decyl, dodecyl, tetradecyl, hexadecyl or octadecyl.
  • alkylene means in general linear or branched C 1 -C 18 alkylene, wherein examples of preferred linear representatives are for example —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 6 —, —(CH 2 ) 7 —, —(CH 2 ) 8 —, —(CH 2 ) 9 —, —(CH 2 ) 10 —, —(CH 2 ) 11 —, —(CH 2 ) 12 —, —(CH 2 ) 13 —, —(CH 2 ) 14 —, —(CH 2 ) 15 —, —(CH 2 ) 16 —, —(CH 2 ) 17 —, —(CH 2 ) 18 —, preferably C 4 -C 16 alkylene such as —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 6 —, —(CH 2 ) 7 —,
  • alkoxy group in C 1 -C 18 alkoxy or in C 1 -C 18 alkoxycarbonyl can be linear or branched and is for example methoxy, ethoxy, n-propoxy, isopropoxy, butyloxy, hexyloxy, decyloxy, dodecyloxy, hexadecyloxy or octadecyloxy, preferably C 1 -C 8 alkoxy such as methoxy, ethoxy, n-propoxy, isopropoxy, butyloxy, hexyloxy, or octyloxy.
  • C 1 -C 18 alkylmercapto is, for example, methylmercapto, ethylmercapto, propylmercapto, butylmercapto, octylmercapto, decylmercapto, hexadecylmercapto or octadecylmercapto.
  • C 1 -C 18 alkylamino is, both alone and in C 1 -C 18 alkylaminocarbonyl, for example methylamino, ethylamino, propylamino, hexylamino, decylamino, hexadecylamino or octadecylamino, preferably C 1 -C 6 alkylamino such as methylamino, ethylamino, propylamino or hexylamino.
  • C 5 -C 10 cycloalkyl is preferably C 5 -C 7 cycloalkyl, such as, for example, cyclopentyl or cyclohexyl, especially cyclohexyl.
  • C 5 -C 7 cycloalkenyl is mono- or bicyclic cycloalkenyl, for example cyclopentenyl, cyclohexenyl or norbornenyl.
  • C 6 -C 12 aryl is typically phenyl, 1-naphthyl, 2-naphthyl, 4-biphenyl, which may be unsubstituted or substituted by, for example, one or more C 1 -C 4 alkyl groups, C 1 -C 4 alkoxy groups, or halogen atoms.
  • C 7 -C 12 aralkyl is typically benzyl, 2-benzyl-2-propyl, ⁇ -phenyl-ethyl, ⁇ , ⁇ -dimethylbenzyl, ⁇ -phenyl-butyl, or ⁇ , ⁇ -dimethyl- ⁇ -phenyl-butyl, in which both the aliphatic hydrocarbon group and aromatic hydrocarbon group may be unsubstituted or substituted substituted by, for example, one or more C 1 -C 4 alkyl groups, C 1 -C 4 alkoxy groups, or halogen atoms.
  • alkylene (spacer) is typically C 1 -C 30 alkylene, preferably C 1 -C 18 alkylene, and embraces the linear as well as the branched representatives and can be, for example, —CH 2 — and C 2 -C 30 alkylene, such as —(CH 2 ) 2 —, —CH(Me)—, —(CH 2 ) 3 —, —CH 2 —CH(Me)—, —C(Me) 2 —, —(CH 2 ) 4 —, —(CH 2 ) 5 —, —(CH 2 ) 6 —, —(CH 2 ) 7 —, —(CH 2 ) 8 —, —(CH 2 ) 9 —, —(CH 2 ) 10 —, —(CH 2 ) 11 —, —(CH 2 ) 12 —, —(CH 2 ) 13 —, —(CH 2 ) 14 —, —(CH 2 ) 2
  • alkylene spacer can optionally comprise one or more, in particular one or two groups selected from —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— as linking group.
  • C 1 -C 30 alkylene can, for example, be interrupted several times by —O—, —S—, —NH— or —C(O)NH—, such as —(CH 2 ) 2 —O—(CH 2 )—, —(CH 2 ) 2 —O—(CH 2 ) 2 —, —(CH 2 ) 2 —S—(CH 2 ) 2 —, —CH 2 —CH—CH 2 —O—(CH 2 ) p —CH 3 , wherein p is an integer from 1 to 10; or —CHX 13 CH 2 —(X 14 ) n —OH, wherein X 13 is C 1 -C 8 alkyl, X 14 is an alkylene oxide monomer, preferably ethylene oxide or propylene oxide, or alkylene amino monomer, preferably amino ethylene or amino propylene, and n is an integer from 1 to 10, preferably 1 to 5; or —(CH 2 ) 2 —NH—(
  • “Arylene (spacer)” is an unsubstituted or substituted carbocylic or heterocyclic arylene group, preferably containing 6 to 14 carbon atoms, typically phenylene, naphthylene, anthracenylene, anthraquinonylene, pyridinylene, quinolinylene, preferably a group wherein X 11 is a single bond in ortho-, meta- or para-position, or —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— in ortho-, meta- or para-position; para-phenylene and para-phenylenoxy are preferred.
  • “Aralkylene (spacer)” is an unsubstituted or substituted carbocylic or heterocyclic aralkylene group, preferably containing 6 to 14 carbon atoms, preferably a group wherein X 11 is a single bond in ortho-, meta- or para-position, or —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— in ortho-, meta- or para-position, and X 12 is alkylene, or a group wherein X 12 is alkylene in ortho-, meta- or para-position and X 11 is a single bond, —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or COO—.
  • Cycloalkylene (spacer) is an unsubstituted or substituted carbocylic or heterocyclic cycloalkylene group, preferably containing 6 to 14 carbon atoms, typically cyclohexylene, preferably a group xii wherein X 11 is a single bond in 2-, 3- or 4-position, or —O—, —S—, —NR 14 —, —CO—, —CONH—, —CONR 15 —, or —COO— in 2-, 3- or 4-position; 4-cyclohexylene and 4-cyclohexylenoxy are preferred.
  • the diketopyrrolopyrroles of the general formula IV and V are new.
  • another aspect of the present invention is directed to new diketopyrrolopyrroles.
  • R 1 is R 2
  • R 3 is R 4 in formula IV
  • R 21 is R 22
  • R 23 is R 24 in formula V.
  • the sum of the number of carbon atoms of R 1 and R 3 (as well as R 2 and R 4 ) and R 21 and R 23 (as well as R 22 and R 24 ) is preferably 12 ⁇ 6, most preferred 12 ⁇ 4.
  • R 3 and R 4 are preferably identical and are C 1 -C 16 alkyl, C 1 -C 16 alkoxy, —NR 16 R 17 , —CONHR 18 , or —SO 2 NH—R 20 , wherein R 18 and R 17 are independently of each other both C 1 -C 16 alkyl or one of the groups R 16 and R 17 is hydrogen and the other is C 1 -C 16 alkyl, R 18 , R 19 and R 20 are C 1 -C 16 alkyl, and R 18 is C 1 -C 15 alkyl;
  • the diketopyrrolopyrroles are known or can be prepared according to known procedures, see for example: EP-A-61426, EP-A-94911, WO99/54332, WO00/14126, EP-A-787 730 and EP-A-787 730.
  • diketopyrrolopyrroles of the general formula I, especially IV and V show fluorescence (photoluminescence).
  • Said diketopyrrolopyrroles can be used in certain full-color OLED displays with one or few luminescent materials as color changing materials (instead of color filters).
  • Color changing materials work by absorbing light of shorter wavelength (e. g., blue light) and then emitting light of longer wavelength by fluorescence (photoluminescence) (e. g., red or green light).
  • fluorescence photoluminescence
  • the use of color changing materials is known in the art (see e. g., U.S. Pat. No. 5,126,214 (Idemitsu Kosan Co., Ltd.) and U.S. Pat. No. 5,294,870 (Eastman Kodak Co.)).
  • the diketopyrrolopyrroles (DPPs) IV or V can also be used for the preparation of polymers.
  • the polymerisation of the inventive DPPs IV or V is usually carried out in a manner known per se, if desired in the presence of a suitable, preferably customary, comonomer carrying e.g. at least one carbon-carbon double bond or of a polymer carrying polyreactive groups.
  • coloured (co-)polymers can be prepared by polyreacting a mixture consisting of novel DPP monomers and other customary and suitable copolymerisable monomers in liquid phase such as in a melt, solution, suspension and emulsion.
  • Suitable copolymerisable monomers to be mentioned are, for example, the group of the acrylates, methacrylates and other customary vinylic monomers such as styrene and its customary monomer derivatives or 2-N-vinylpyrrolidone.
  • acrylates are monofunctional acrylates such as butanediolmonoacrylate, 2-hydroxyethylacrylate, butylacrylate, 2-ethylhexylacrylate, phenoxyethylacrylate, tetrahydrofurfurylacrylate, polypropylene glycol monoacrylate, bifunctional acrylates such as 1,6-hexanedioldiacrylate, tripropylene glycol diacrylate, polyethylene glycol(200) diacrylate and polyethylene glycol(400) diacrylate, ethoxylated and propoxylated neopentyl glycol diacrylate, polyfunctional acrylates such as trimethylolpropanetriacrylate, pentaerythritoltriacrylate, ethoxylated or propoxylated trimethylolpropanetriacrylate, propoxylated glycerol triacrylate, tris(2-hydroxyethyl) isocyanurate triacrylate as well as their mixtures with one
  • novel DPP polymers are usually prepared by commonly known methods, e.g. either by a polyreaction, i.e. by polymerisation (thermal or photochemical), polycondensation or polyaddition, or by a polymer-analogous reaction, i.e. by reacting the novel DPP compounds containing suitable reactive groups with polymers already obtained which in turn contain reactive groups (grafting).
  • Photochemical polymerisation is preferred, especially if Q is an acrylic or methacrylic radical.
  • DPP monomers which contain amino and hydroxy groups can also be reacted with an polyisocyanate to prepare a monomeric or polymeric isocyanate, which can be reacted with one or more hydroxy-functional acrylates or (meth)acrylates) to obtain DPP compounds having groups —OC(O)—N—X 4 —N—C(O)—O—X 5 —O—C(O)—C(R 12 ) ⁇ CH 2 .
  • polyisocyanates are aliphatic diisocyanates, such as trimethylene diisocyanate, tetramethylene diisocyanate, hexamethylene diisocyanate, pentamethylene diisocyanate, 1,2-dipropylene diisocyanate, 2,4,4- or 2,2,4-trimethylhexamethylene diisocyanate, and aromatic polyisocyanates, such as m-phenylene diisocyanate, p-phenylene diisocyanate, 4,4′-diphenyl diisocyanate, 1,5-naphthalene diisocyanate, 4,4′-diphenylmethane diisocyanate, 2,4- or 2,6-tolylene diisocyanate, 4,4′-toluidine diisocyanate and 4,4′-diphenyl ether diisocyanate, and alicyclic diisocyanates, such as 1,3- or 1,4-cyclohexane diisocyanate, isophorone
  • hydroxy-functional (meth)acrylates are 2-hydroxyethyl(meth)acrylate, 2-hydroxypropyl(meth)acrylate, 2- or 4-hydroxybutyl(meth)acrylate, pentandiol mono(meth)acrylate, trimethylolpropane di(meth)acrylate, and pentaerythritol tri(meth)acrylate.
  • Typical examples of the preparation of DPP polymers are (a) the polymerisation for the preparation of DPP polyacrylates or polymethacrylates by radical thermal polymerisation of DPP acrylates or DPP methacrylates, i.e.
  • DPPs of formula IV or V containing an acrylic or methacrylic group, or the radical photopolymerisation of DPP acrylates or DPP methacrylates (b) the polycondensation for the preparation of DPP-containing polyesters from DPPs of formula IV or V containing a hydroxy group, or the preparation of DPP polycarbonates from DPP diols and phosgene, (c) the polyaddition for the preparation of DPP polyurethanes from DPP diols and diisocyanates, and also (d) the polymer-analogous reaction, e.g. the reaction of a DPP alcohol with a polymer prepared from styrene and maleic acid anhydride, which thus contains anhydride groups, to a polymer containing DPP mono- or diester groups.
  • the polymer-analogous reaction e.g. the reaction of a DPP alcohol with a polymer prepared from styrene and maleic acid anhydride, which thus contains an
  • the novel DPP polymers also contain additives, such as light stabilisers, antioxidants and UV absorbers, which may be added during or after the actual polymerisation, e.g. also during the processing of the polymers (extrusion).
  • additives can themselves also contain polyreactive groups and can in this case be copolymerised together with the DPP monomers IV or V.
  • the polymerisation can be carried out e.g. photochemically, one of the customary photoinitiators (see e.g. “Chemistry & Technology of UV & EB Formulations for Coatings, Inks and Paints, Vol. 3: Photoinitiators for Free Radical and Cationic Polymerization” 1991, p. 1115-325) usually being added to the reaction mixture in an amount in the range from typically 0.5 to 5% by weight, based on the sum of all monomers used.
  • Another preferred embodiment of this invention thus relates to polymers based on the diketopyrrolopyrroles IV or V, which are obtainable by polyreacting a mixture consisting of
  • Another embodiment of this invention relates to the use of the novel mixture for the preparation of polymers.
  • this invention relates to the use of polymers prepared according to this invention for colouring high molecular weight organic materials, for formulations of decorative cosmetics, for the production of inks, printing inks, paint systems, in particular automotive lacquers and photosensitive coatings, photo- and electroconducting polymers, fluorescent brighteners, photocell aggregates, coloured photoresists and dispersion paints.
  • the DPP polymers prepared according to this invention are particularly suitable for colouring high molecular weight organic materials, such as biopolymers, plastic materials, including fibres, glasses, ceramic products, for formulations of decorative cosmetics, for the preparation of inks, printing inks, paint systems, in particular automotive lacquers and photosensitive coatings, photo- and electroconducting polymers, fluorescent brighteners, photocell aggregates, coloured photoresists and dispersion paints, and the diketopyrrolopyrroles of this invention can also be used in the biomedical field, for example for the preparation of diagnostic agents, and in the fields of impact and non impact printing and photo/repro in general.
  • organic materials such as biopolymers, plastic materials, including fibres, glasses, ceramic products, for formulations of decorative cosmetics, for the preparation of inks, printing inks, paint systems, in particular automotive lacquers and photosensitive coatings, photo- and electroconducting polymers, fluorescent brighteners, photocell aggregates, coloured photoresists and
  • Suitable high molecular weight organic materials which can be coloured with the novel DPP polymers, are vinyl polymers, such as polystyrene, poly- ⁇ -methylstyrene, poly-p-methylstyrene, poly-p-hydroxystyrene, poly-p-hydroxyphenylstyrene, polymethyl methacrylate and polyacrylamide as well as the corresponding methacrylic compounds, polymethylmaleate, polyacrylonitrile, polymethacrylonitrile, polyvinyl chloride, polyvinyl fluoride, polyvinylidene chloride, polyvinylidene fluoride, polyvinyl acetate, polymethyl vinyl ether and polybutyl vinyl ether; polymers derived from maleinimide and/or maleic anhydride, such as copolymers of maleic anhydride with styrene; polyvinyl pyrrolidone; ABS; ASA; polyamides; polyimides; polyamidimides; polys
  • Particularly preferred high molecular weight organic materials are e.g. cellulose ethers and cellulose esters, such as ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate, natural resins or synthetic resins (polymerisation or condensation resins), such as aminoplasts, in particular urea/formaldehyde resins and melamine/formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polyamides, polyurethanes, polyesters, ABS, ASA, polyphenylene oxides, rubber, casein, silicone and silicone resins as well as their possible mixtures with one another.
  • cellulose ethers and cellulose esters such as ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate
  • natural resins or synthetic resins such as aminoplasts, in particular urea/formaldehyde resins and mel
  • organic materials in dissolved form as film formers, such as boiled linseed oil, nitrocellulose, alkyd resins, phenolic resins, melamine/formaldehyde resins and urea/formaldehyde resins and also acrylic resins.
  • film formers such as boiled linseed oil, nitrocellulose, alkyd resins, phenolic resins, melamine/formaldehyde resins and urea/formaldehyde resins and also acrylic resins.
  • the cited high molecular weight organic compounds can be used singly or in mixtures, e.g. as granulates, plastic compounds, melts or in the form of solutions, in particular for the preparation of spinning solutions, paint systems, coating compositions, inks or printing inks.
  • the novel DPP polymers are used for mass colouring polyvinyl chloride, polyamides and, in particular, polyolefins such as polyethylene and polypropylene, and for the preparation of paint systems, including powder coatings, inks, printing inks and paints.
  • binders for paint systems to be mentioned are alkyd/melamine surface coating resins, acryl/melamine surface coating resins, cellulose acetate/cellulose butyrate paints and two-component paints based on acrylic resins crosslinkable with polyisocyanate.
  • the novel DPP polymers can be added to the material to be coloured in any desired amount, depending on the end use requirements.
  • the novel DDP polymers can be used in amounts in the range from 0.01 to 40, preferably from 0.1 to 20% by weight, based on the total weight of the high molecular weight organic material.
  • the high molecular weight organic materials are normally coloured with the novel DPP polymers such that said polymers, if desired in the form of masterbatches, are admixed to the high molecular weight organic materials using customary suitable appliances, for example extruders, roll mills, mixing or milling apparatus.
  • the material thus treated is then usually brought into the desired final form by methods known per se, such as calendering, moulding, extruding, coating, casting or injection moulding.
  • DDPs of formual IV or V containing photocurable groups such as acrylate or methacrylate groups in other photocurable monomers, either with or without solvent, in the latter case e.g. by melting and dissolving, and then to mix them with corresponding photoinitiators and to coat suitable substrates therewith, the coatings being cured, i.e. polymerised, by means of actinic radiation, preferably UV radiation.
  • novel DPP monomers can be poly-reacted in an extruder together with other monomers, in particular those customarily used for the preparation of the above-mentioned polymers (reactive extrusion, in analogy to the process described, inter alia, in EP-A 337 951).
  • Copolymers prepared in this manner usually have the same spectrum of use as the blends of novel DPP polymers and high molecular weight organic materials mentioned so far.
  • novel DPP polymers can be advantageously added in admixture with fillers, transparent and opaque white, coloured and/or black pigments and conventional luster pigments in the desired amount.
  • coating compositions, inks and printing inks, the corresponding high molecular weight organic substances, such as binders, synthetic resin dispersions and the like, and the novel DPP compounds or polymers are usually dispersed or dissolved, if desired together with customary additives, such as fillers, paint auxiliaries, siccatives, plasticisers and/or additional pigments, in a shared solvent or solvent mixture.
  • customary additives such as fillers, paint auxiliaries, siccatives, plasticisers and/or additional pigments, in a shared solvent or solvent mixture.
  • This may be effected by dispersing or dissolving the individual components by themselves or also several together and only then bringing all the components together, or by adding all of them in one go.
  • all conventional industrial printing methods may be used, such as screen printing, rotogravure, bronze printing, flexographic printing and offset printing.
  • This invention accordingly relates in another of its embodiments to coloured high molecular weight organic materials prepared by using the polymers according to this invention, to formulations of decorative cosmetics, inks, printing inks, paint systems, in particular automotive lacquers and photosensitive coatings, photo- and electroconducting polymers, fluorescent brighteners, photocell aggregates, coloured photoresists and dispersion paints, preferably to coloured high molecular weight organic materials and paint systems, particularly preferably to automotive paints and photosensitive coatings.
  • the polymers and copolymers prepared according to this invention and based on the novel DPP monomers IV or V show excellent migration and fastness characteristics and have high transparence and pure hue as compared to the corresponding polymers of the state of the art.

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US10/522,212 2002-07-22 2003-07-15 Polymerisable diketopyrrolopyrroles, use of such compounds in colour filters and polymers prepared from these compounds Abandoned US20050255391A1 (en)

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Publication number Priority date Publication date Assignee Title
US20090140220A1 (en) * 2007-11-30 2009-06-04 Cheil Industries Inc. Photosensitive Resin Composition for Color Filter and Color Filter Using Same
US20090208854A1 (en) * 2006-11-17 2009-08-20 Cheil Industries Inc. Photosensitive Resin Composition for Forming Column Spacer of Liquid Crystal Display, Method for Forming Column Spacer Using the Composition, Column Spacer Formed by the Method, and Display Device Comprising the Column Spacer
US20140306212A1 (en) * 2011-11-15 2014-10-16 Basf Se Organic semiconductor device and process for its production
WO2017202635A1 (en) 2016-05-25 2017-11-30 Basf Se Semiconductors
EP3810696A2 (en) * 2018-06-25 2021-04-28 Basf Se Red pigment composition for color filter
CN117826454A (zh) * 2023-12-22 2024-04-05 武汉华星光电技术有限公司 显示面板及显示装置

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* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
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JP2007095162A (ja) * 2005-09-28 2007-04-12 Hitachi Global Storage Technologies Netherlands Bv 磁気記録媒体及びその製造法
FR2956028B1 (fr) 2010-02-08 2012-03-02 Oreal Composition cosmetique incluant au moins un compose fluorophore.
JP2011153278A (ja) * 2010-01-28 2011-08-11 Fujifilm Corp 顔料微粒子分散体及び光硬化性組成物、これに用いられる新規化合物
CN107840848A (zh) * 2016-09-18 2018-03-27 南京工业大学 一类吡咯并吡咯二酮聚醚衍生物及其制备方法
CN110791117A (zh) * 2018-08-01 2020-02-14 浙江浩川科技有限公司 一种芳香亚胺基取代的dpp类有机颜料及合成方法和用途
CN109897043B (zh) * 2019-03-29 2021-08-13 华东理工大学 含氟吡咯并吡咯二酮季铵盐类化合物及其制备方法与应用
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JP6928755B1 (ja) * 2020-03-13 2021-09-01 東洋インキＳｃホールディングス株式会社 顔料分散剤、カラーフィルタ用顔料組成物、着色組成物、およびカラーフィルタ
CN116813625A (zh) * 2023-06-29 2023-09-29 贵州民族大学 一种具有高荧光量子产率的吡咯并吡咯二酮有机染料及其制备方法
CN116969952A (zh) * 2023-07-31 2023-10-31 山东凯瑞尔光电科技有限公司 一种二苯基吡咯并吡咯二酮衍生物及其颜料组合物

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5750723A (en) * 1996-01-30 1998-05-12 Ciba Specialty Chemicals Corporation Polymerizable diketopyrrolopyrroles and polymers prepared therewith
US5847156A (en) * 1996-01-03 1998-12-08 Ciba Specialty Chemicals Corporation Polymerizable diketopyrrolopyrroles and polymers prepared therewith
US5919944A (en) * 1997-07-30 1999-07-06 Ciba Specialty Chemicals Corporation Polymerisable diketopyrrolopyrroles
US6107491A (en) * 1998-07-20 2000-08-22 Ciba Specialty Chemicals Corporation Polymerizable diketopyrrolopyrroles

Family Cites Families (9)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0337951A3 (de) * 1988-04-15 1991-04-24 Ciba-Geigy Ag Farbige Polymermikropartikel
EP0648770B1 (de) * 1993-10-13 2000-05-17 Ciba SC Holding AG Pyrrolo[3,4-c]pyrrole
EP0654711B1 (en) * 1993-11-22 1999-06-02 Ciba SC Holding AG Compositions for making structured color images and application thereof
EP0811625B1 (en) * 1996-06-05 2002-04-17 Ciba SC Holding AG Process for preparing diketopyrrolopyrrole derivatives
US5947156A (en) * 1997-03-11 1999-09-07 Tomczyk; Frederick A. Holding tank having waste evacuation device
EP0952183B1 (de) * 1998-04-22 2005-02-23 Ciba SC Holding AG Verzugsfreie Pigmentzusammensetzungen enthaltend Diaryl-diketopyrrolo 3,4c pyrrole
AU754087B2 (en) * 1998-04-22 2002-11-07 Ciba Specialty Chemicals Holding Inc. Preparation of alkylthio- and/or arylthio-substituted diketo-diaryl-pyrrolopyrroles
TWI290164B (en) * 1999-08-26 2007-11-21 Ciba Sc Holding Ag DPP-containing conjugated polymers and electroluminescent devices
TW593567B (en) * 2000-07-31 2004-06-21 Ciba Sc Holding Ag Dispersant compositions improving the heat stability of transparent pigments

Patent Citations (5)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5847156A (en) * 1996-01-03 1998-12-08 Ciba Specialty Chemicals Corporation Polymerizable diketopyrrolopyrroles and polymers prepared therewith
US5750723A (en) * 1996-01-30 1998-05-12 Ciba Specialty Chemicals Corporation Polymerizable diketopyrrolopyrroles and polymers prepared therewith
US6048918A (en) * 1996-01-30 2000-04-11 Ciba Specialty Chemicals Corporation Polymerizable diketopyrrolopyrroles and polymers prepared therewith
US5919944A (en) * 1997-07-30 1999-07-06 Ciba Specialty Chemicals Corporation Polymerisable diketopyrrolopyrroles
US6107491A (en) * 1998-07-20 2000-08-22 Ciba Specialty Chemicals Corporation Polymerizable diketopyrrolopyrroles

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20090208854A1 (en) * 2006-11-17 2009-08-20 Cheil Industries Inc. Photosensitive Resin Composition for Forming Column Spacer of Liquid Crystal Display, Method for Forming Column Spacer Using the Composition, Column Spacer Formed by the Method, and Display Device Comprising the Column Spacer
US20090140220A1 (en) * 2007-11-30 2009-06-04 Cheil Industries Inc. Photosensitive Resin Composition for Color Filter and Color Filter Using Same
US8158036B2 (en) * 2007-11-30 2012-04-17 Cheil Industries Inc. Photosensitive resin composition for color filter and color filter using same
TWI385483B (zh) * 2007-11-30 2013-02-11 Cheil Ind Inc 彩色濾光器用之光感應性樹脂組成物以及使用該組成物的彩色濾光器
US20140306212A1 (en) * 2011-11-15 2014-10-16 Basf Se Organic semiconductor device and process for its production
US9543521B2 (en) * 2011-11-15 2017-01-10 Basf Se Organic semiconductor device and process for its production
WO2017202635A1 (en) 2016-05-25 2017-11-30 Basf Se Semiconductors
US11384197B2 (en) 2016-05-25 2022-07-12 Clap Co., Ltd. Semiconductors
EP3810696A2 (en) * 2018-06-25 2021-04-28 Basf Se Red pigment composition for color filter
CN117826454A (zh) * 2023-12-22 2024-04-05 武汉华星光电技术有限公司 显示面板及显示装置

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KR101011941B1 (ko) 2011-02-08
AU2003257464A1 (en) 2004-02-09
EP1523528B1 (en) 2012-02-22
TWI269072B (en) 2006-12-21
KR20050023458A (ko) 2005-03-09
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ATE546497T1 (de) 2012-03-15
US7723530B2 (en) 2010-05-25
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