WO2007003520A1 - Dicétopyrrolopyrroles et dérivés fluorescents - Google Patents

Dicétopyrrolopyrroles et dérivés fluorescents Download PDF

Info

Publication number
WO2007003520A1
WO2007003520A1 PCT/EP2006/063527 EP2006063527W WO2007003520A1 WO 2007003520 A1 WO2007003520 A1 WO 2007003520A1 EP 2006063527 W EP2006063527 W EP 2006063527W WO 2007003520 A1 WO2007003520 A1 WO 2007003520A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
alkyl
substituted
aryl
alkoxy
Prior art date
Application number
PCT/EP2006/063527
Other languages
English (en)
Inventor
Hidetaka Oka
Hiroshi Yamamoto
Junichi Tanabe
Original Assignee
Ciba Specialty Chemicals Holding Inc.
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Ciba Specialty Chemicals Holding Inc. filed Critical Ciba Specialty Chemicals Holding Inc.
Publication of WO2007003520A1 publication Critical patent/WO2007003520A1/fr

Links

Classifications

    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K8/00—Cosmetics or similar toiletry preparations
    • A61K8/18—Cosmetics or similar toiletry preparations characterised by the composition
    • A61K8/72—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds
    • A61K8/84—Cosmetics or similar toiletry preparations characterised by the composition containing organic macromolecular compounds obtained by reactions otherwise than those involving only carbon-carbon unsaturated bonds
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61Q—SPECIFIC USE OF COSMETICS OR SIMILAR TOILETRY PREPARATIONS
    • A61Q19/00—Preparations for care of the skin
    • 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
    • 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
    • C08G61/025—Polyxylylenes
    • 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
    • C08G61/10—Macromolecular compounds containing only carbon atoms in the main chain of the macromolecule, e.g. polyxylylenes only aromatic carbon atoms, e.g. polyphenylenes
    • 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
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/124—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one nitrogen atom in the ring
    • 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
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C08G61/122—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides
    • C08G61/123—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds
    • C08G61/126—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule derived from five- or six-membered heterocyclic compounds, other than imides derived from five-membered heterocyclic compounds with a five-membered ring containing one sulfur atom in the ring
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0605—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0611—Polycondensates containing five-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polypyrroles
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0622—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0627—Polycondensates containing six-membered rings, not condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/0683—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms
    • C08G73/0688—Polycondensates containing six-membered rings, condensed with other rings, with nitrogen atoms as the only ring hetero atoms with only one nitrogen atom in the ring, e.g. polyquinolines
    • 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
    • C08G73/00—Macromolecular compounds obtained by reactions forming a linkage containing nitrogen with or without oxygen or carbon in the main chain of the macromolecule, not provided for in groups C08G12/00 - C08G71/00
    • C08G73/06—Polycondensates having nitrogen-containing heterocyclic rings in the main chain of the macromolecule
    • C08G73/08—Polyhydrazides; Polytriazoles; Polyaminotriazoles; Polyoxadiazoles
    • 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
    • A—HUMAN NECESSITIES
    • A61—MEDICAL OR VETERINARY SCIENCE; HYGIENE
    • A61K—PREPARATIONS FOR MEDICAL, DENTAL OR TOILETRY PURPOSES
    • A61K2800/00—Properties of cosmetic compositions or active ingredients thereof or formulation aids used therein and process related aspects
    • A61K2800/40—Chemical, physico-chemical or functional or structural properties of particular ingredients
    • A61K2800/42—Colour properties
    • A61K2800/43—Pigments; Dyes
    • A61K2800/434—Luminescent, Fluorescent; Optical brighteners; Photosensitizers
    • 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
    • C08G2261/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G2261/30—Monomer units or repeat units incorporating structural elements in the main chain
    • C08G2261/34—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain
    • C08G2261/342—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms
    • C08G2261/3424—Monomer units or repeat units incorporating structural elements in the main chain incorporating partially-aromatic structural elements in the main chain containing only carbon atoms non-conjugated, e.g. paracyclophanes or xylenes
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C09K2211/1033—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom with oxygen
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1044—Heterocyclic compounds characterised by ligands containing two nitrogen atoms as heteroatoms
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1088—Heterocyclic compounds characterised by ligands containing oxygen as the only heteroatom

Definitions

  • the present invention relates to fluorescent diketopyrrolopyrroles (DPPs) and derivatives of the formula
  • a luminescent device comprising a compound according to the present invention is high in the efficiency of electrical energy utilisation and high in luminance, preferably with a blue to greenish blue emission.
  • US-B-4,778,899 relates to a process for the preparation of DPPs of the formula I, wherein X and Y are -NH, and A 1 and A 2 are independently of each other an alkyl or aralkyl group or an isocyclic or heterocyclic aromatic radical.
  • X and Y are -NH
  • a 1 and A 2 are independently of each other an alkyl or aralkyl group or an isocyclic or heterocyclic aromatic radical.
  • alkyl-substituted pyrrolopyrroles are explicitly mentioned:
  • JP-A2 9003448 (Toyo) describes an organic EL element having between a pair of electrodes a luminous layer containing a DPP-compound as electron-transporting material or an organic compound thin film layer including a luminous layer and an electron-injecting layer wherein the electron-injecting layer contains a DPP compound as the electron-transporting material.
  • the following three heteroarylpyrrolopyrroles are explicitly mentioned:
  • luminescent devices which are high durability besides high in the efficiency of electrical energy utilisation and high in luminance, can be obtained if specific DPP compounds or specific combinations of DPP compounds are used, especially as light emitting substances.
  • the present invention relates to fluorescent compounds of the formula
  • R 1 and R 2 may be the same or different and are selected from a C 1 -C 25 alkyl group, which can optionally be interrupted by one or more oxygen atoms and/or can optionally be substituted by a hydroxyl group, an alkoxy group or an amino group; an allyl group, which can be substituted one to three times with C 1 -C 3 alkyl, a cycloalkyl group, which can optionally be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy, a cycloalkyl group, which is condensed one or two times by phenyl which can be substituted one to three times with C 1 -C 4 -alkyl, halogen, nitro, or cyano; an alkenyl group, a cycloalkenyl group, an alkynyl group, a hetero
  • R 5 , R 6 , R 7 , R 5 , R 6 and R 7 may be the same or different and are selected from hydrogen, C 1 - C 25 alkyl, which optionally can be substituted by a hydroxyl group, an alkoxy group, an amino group, a heterocyclic group, a ketone or aldehyde group, an ester group, a carbamoyl group, a silyl group, a siloxanyl group, aryl, or heteroaryl; cycloalkyl, especially cvclohexyl, which can optionally be substituted by one, or two C 1 -C 8 alkyl groups, or C 6 -Ci 4 aryl groups, especially phenyl, or naphthyl, which can optionally be substituted by one, or two C 1 -C 8 alkyl groups, cycloalkyl, which is condensed one or two times by phenyl which can be substituted one to three times with C 1 -C 4 -
  • a 2 , A 4 and A 6 stand independently of each other for A 1 , an unsubstituted, or substituted aryl group, or a unsubstituted, or substituted heteroaryl group.
  • a 7 isalkylene, alkenylene, alkynylene, allylene, arylene, or heteroarylene, which is optionally substituted one to three times with C 1 -C 8 -alkyl, or C 1 -C 8 -alkoxy, with the proviso that the following compounds of formula I are excluded, wherein X and Y are N-R 1 and N-R 2 , respectively:
  • EL devices employing a DPP of formula I, Il and/or III as light emitting materials can show advanced performance (EL intensity; chromaticity for blue emission at shorter wavelength ( ⁇ 500 nm)).
  • X is -N-R 1 and Y is -N-R 2 , at least one of R 1 and R 2 , preferably both of R 1 and R 2 are different from a hydrogen atom.
  • R 1 and R 2 independently from each other stand, preferably, for C 1 -C 8 alkyl, C 5 -Ci 2 -cycloalkyl, which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy, phenyl or 1- or 2-naphthyl which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy, or -CR 3 R 4 -(CH 2 ) m -A 3 , wherein R 3 and R 4 stand for hydrogen, or C 1 -C 4 alkyl, A 3 stands for phenyl or 1- or 2-naphthyl, which can be substituted one to three times with C 1 -C 8 alkyl and/or C 1 -C 8 alkoxy, and m stands for 0 or 1 , especially C 1 -C 8 alkyl, such as methyl, ethyl, n-propyl
  • R 1 and R 2 are the same and stand for C 1 -C 8 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2- dimethylpropyl, n-hexyl, n-heptyl, n-octyl, 1,1,3,3-tetramethylbutyl and 2-ethylhexyl.
  • C 1 -C 8 alkyl such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2- dimethylpropyl, n-hexyl, n-hepty
  • a 1 , A 3 and A 5 stand, preferably, independently of each other for cycloalkyl, especially cyclohexyl, which can optionally be substituted by one, or two C 1 -C 8 alkyl groups, or phenyl groups, which can optionally be substituted by one, or two C 1 -C 8 alkyl groups, cycloalkyl, which is condensed one or two times by phenyl which can be substituted one to three times with C 1 -C 4 -alkyl, halogen, nitro, or cyano; 2-adamantyl, or 1-adamantyl;
  • R 5' , R 6 and R 7 may be the same or different and are selected from hydrogen, C 1 -C 25 alkyl, cycloalkyl, especially cyclohexyl, which can optionally be substituted by one, or two C 1 -C 8 alkyl groups, or C 6 -Ci 4 aryl groups, especially phenyl, or naphthyl, which can optionally be substituted by one, or two C 1 -C 8 alkyl groups, cycloalkyl, which is condensed one or two times by phenyl which can be substituted one to three times with C 1 - C 4 -alkyl, halogen, nitro, or cyano; 2-adamantyl, or 1-adamantyl; a heterocyclic group, halogen, haloalkyl, or an amino group, which can optionally be substituted by an alkyl group, alkylar ⁇ l group, an aryl group, a heteroaryl group, an hetero
  • a 1 , A 3 and A 5 stand for a group
  • R 5 and R 7 are independently of each other C 1 -
  • R 6 stands for a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group. Examples of such aryl and heteroaryl groups are given below in the description of A 2 , A 4 and A 6 .
  • R 5 and R 7 are preferably different from hydrogen.
  • R 1 and R 2 are independently of each other an aryl group, or a group -CR 3 R 4 -(CH 2 ) m -A 3 , wherein A 3 is an aryl group, especially a polycyclic aryl group and m is 0, or 1. Examples of such aryl groups are given below in the description of A 2 , A 4 and A 6' .
  • a 1 , A 3 and A 5 stand for C 1 -C 25 alkyl, such as methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, n- hexyl, n-heptyl, n-octyl, 1,1,3,3-tetramethylbutyl and 2-ethylhexyl; cycloalkyl, especially cyclohexyl, which can optionally be substituted by one, or two C 1 -C 8 alkyl groups, or phenyl groups, which can optionally be substituted by one, or two C 1 -C 8 alkyl groups, cycloalkyl, which is condensed one or two times by phenyl which can be substituted one to three times
  • C 1 -C 4 -alkyl such as , , , and wherein A 20 and A 21 are independently of each other a substituted or unsubstituted aryl group, or a substituted or unsubstituted heteroaryl group, or 1-adamantyl.
  • aryl and heteroaryl groups are given below in the description of A 2 , A 4 and A 6' .
  • Examples of such aryl substituted cyclohexans are
  • a 2 , A 4 and A 6 stand independently of each other for A 1 .
  • a 2 , A 4 and A 6 stand independently of each other for an unsubstituted, or substituted aryl group, or a unsubstituted, or substituted heteroar ⁇ l group.
  • a 2 , A 4 and A 6 stand, preferably, independently of each other for
  • X is N, or C-R 8 ,
  • R 5 to R 11 may be the same or different and are selected from hydrogen, C 1 -C 25 alkyl, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, a mercapto group, alkoxy, alkylthio, an aryl ether group, an aryl thioether group, aryl, heteroar ⁇ l, a heterocyclic group, halogen, haloalkyl, haloalkenyl, haloalkynyl, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, a group NR 27 R 28 , wherein R 27 and R 28 independently of each other stand for a hydrogen atom, an alkyl group, an optionally substituted cycloalkyl group, an optionally substituted aryl group, an optionally substituted heteroaryl group,
  • a 2 , A 4 and A 6 stand independently of each other for
  • R 101 to R 123 may be the same or different and are selected from hydrogen, C 1 - C 25 alkyl group, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, a mercapto group, alkoxy, alkylthio, an aryl ether group, an aryl thioether group, aryl, a heterocyclic group, halogen, haloalkyl, haloalkenyl, haloalkynyl, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, a group NR 27 R 28 , wherein R 27 and R 28 are as defined above, a nitro group, a silyl group, a siloxanyl group, a substituted or unsubstituted vinyl group, or at least two adjacent substituents R 115 to R
  • R and R are independently of each other a hydrogen atom, a C 1 -C 18 alkyl group, a C 1 -
  • G is C 1 -C 18 alkyl, -OR 325 , -SR 325 , -NR 325 R 326 , -COR 328 , -COOR 327 , -OCOOR 327 , -CONR 325 R 326 ,
  • R 325 and R 326 are independently of each other C 6 -C 18 aryl; C 6 - C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by -0-; or R 325 and R 326 together form a five or six membered ring, in particular
  • R 327 is C 7 -Ci 2 alkylaryl; C 1 -C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by -O-;
  • R 328 is C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl;
  • R 131 to R 152 may be the same or different and are selected from hydrogen, C 1 - C 25 alkyl group, cycloalkyl, aralkyl, alkenyl, cycloalkenyl, alkynyl, hydroxyl, a mercapto group, alkoxy, alkylthio, an aryl ether group, an aryl thioether group, aryl, a heterocyclic group, halogen, haloalkyl, haloalkenyl, haloalkynyl, a cyano group, an aldehyde group, a carbonyl group, a carboxyl group, an ester group, a carbamoyl group, a group NR 27 R 28 , wherein R 27 and R 28 are as defined above, a nitro group, a silyl group, a siloxanyl group, a substituted or unsubstituted vinyl group,
  • R 153 is a hydrogen atom, a C 1 -C 25 alkyl group, which might be interrupted by -O-, a cycloalkyl group, an aralkyl group, an aryl group, or a heterocyclic group.
  • aryl group is typically C 6 -C 3 oaryl, such as phenyl, biphenyl, pentalenyl, indenyl, azulenyl, naphthyl, biphenylenyl, as-indacenyl, s-indacenyl, acenaphthylenyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, acephenanthrylenyl, aceanthrylenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentacenyl, pentaphenyl, hexacenyl, or hexaphenyl, which can optionally be substituted by one, two, or three, preferably C 1 -C 8 alkyl groups, or C 1 -C 8 alkoxy groups.
  • polycyclic aryl group are preferred, such as pentalenyl, indenyl, azulenyl, naphthyl, biphenylenyl, as-indacenyl, s-indacenyl, acenaphthylenyl, fluorenyl, phenanthryl, anthracenyl, fluoranthenyl, acephenanthrylenyl, aceanthrylenyl, triphenylenyl, pyrenyl, chrysenyl, naphthacenyl, picenyl, perylenyl, pentacenyl, pentaphenyl, hexacenyl, or hexaphenyl, which can optionally be substituted by one, two, or three C 1 -C 8 alkyl groups, or C 1 -C 8 alkoxy groups.
  • a , A and A are an aryl group, they stand preferably for
  • R and R are independently of each other ,or wherein R , R JU and R are independently of each other hydrogen, C 1 -C 8 alkyl, C 1 -C 8 alkoxy
  • R 34 is hydrogen, C 1 -C 8 alkyl or C 1 -C 8 alkoxy, or R 27 and R 28 together with the nitrogen atom to which they are bonded form a five or six membered
  • heterocyclic ring such as
  • R 216 and R 217 independently from each other stands for hydrogen, C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, or phenyl, and
  • X 1 stands for hydrogen, or C 1 -C 8 -alkyl
  • R 101 , R 102 , R 103 , R 106 , R 107 , R 110 , R 111 , R 112 , R 115 , R 116 , R 122 , R 123 , R 135 , R 136 , or R 137 are independently of each other hydrogen, C 1 -C 8 alkyl, a hydroxyl group, a mercapto group, C 1 -
  • R 124 and R 125 may be the same or different and are selected from C 1 -C 18 alkyl; or R 124 and
  • R 125 together form a ring, especially a five-, six- or seven-membered ring, which can optionally be substituted by C 1 -C 8 alkyl, or which can optionally be condensed one or two times by phenyl which can be substituted one to three times with C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen and cyano; and
  • R 251 , R 252 , R 253 , R 254 , R 255 and R 256 are independently of each other C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy,
  • R 300 is C 1 -
  • R 115 is hydrogen, phenyl, or 1-naphthyl, which can be substituted by one, or more C 1 -C 8 alkyl, or C 1 -C 8 alkoxy groups; C 1 -C 8 alkyl, or C 1 -C 8 alkoxy, R 124 and R 125 are C 1 -C 8 alkyl or C 1 -C 8 alkoxy, and R 30 is hydrogen, C 1 -C 8 alkyl or C 1 -C 8 alkoxy.
  • R 124 and R 125 together form a ring, they form preferably a cyclopentane, or cyclohexane ring, which can optionally be substituted by one to three times with C 1 -C 8 alkyl, or which can optionally be condensed one or two times by phenyl which can be substituted one to three times with C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen and cyano. Examples of condensed cyclopentyl
  • R 251 , R 252 , R 253 , R 254 , R 255 and R 256 are independently of each other C 1 -C 8 -alkyl, C 1 -C 8 -alkoxy, halogen and cyano, in particular hydrogen.
  • heteroaryl or heterocyclic group is a ring with five to seven ring atoms, wherein nitrogen, oxygen or sulfur are the possible hetero atoms, and is typically an unsaturated heterocyclic radical with five to 18 atoms having at least six conjugated ⁇ -electrons such as thienyl, benzo[b]thienyl, dibenzo[b,d]thienyl, thianthrenyl, furyl, furfuryl, 21-l-pyranyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, phenoxythienyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, bipyridyl, triazinyl, pyrimidinyl, pyrazinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinoliziny
  • a 2 , A 4 and A 6 are derived from a heteroaryl group, they are preferably a group of formula
  • A' is preferably a single bond, -CO-, -COO-, -S-, -SO-, -SO 2 -, -0-, -(CA 14 A 15 ) n8 -
  • n1, n2, n3, n4, n5, n6 and n7 are integers of 1 to 10, in particular 1 to 3, n8 is an integer of 1 to 10,
  • a 6 and A 7 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by
  • C 20 heteroaryl C 2 -C 20 heteroaryl which is substituted by G', C 2 -Ci 8 alkenyl, C 2 -Ci 8 alkynyl, C 1 - C 18 alkoxy, C 1 -C 18 alkoxy which is substituted by E' and/or interrupted by D', C 7 -C 25 aralkyl, or -
  • a 8 is C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E' and/or interrupted by D', C 6 -C 24 aryl, or C 7 -C 25 aralkyl,
  • a 9 and A 10 are independently of each other C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E' and/or interrupted by D', C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G', C 2 -C 20 heteroaryl,
  • C 2 -C 20 heteroaryl which is substituted by G', C 2 -Ci 8 alkenyl, C 2 -Ci 8 alkynyl, C 1 -C 18 alkoxy, C 1 - C 18 alkoxy which is substituted by E' and/or interrupted by D', or C 7 -C 25 aralkyl, or
  • a 9 and A 10 form a ring, especially a five- or six-membered ring, which can optionally be substituted by one or more C 1 -C 18 alkyl groups;
  • a 14 and A 15 are independently of each other H, C 1 -C 18 alkyl, C 1 -C 18 alkyl which is substituted by E' and/or interrupted by D', C 6 -C 24 aryl, C 6 -C 24 aryl which is substituted by G', C 2 -
  • E' is -OA 29 ; -SA 29 ; -NA 25 A 26 ; -COA 28 ; -COOA 27 ; -CONA 25 A 26 ; -CN; -OCOOA 27 ; or halogen;
  • G' is E', or C 1 -C 18 alkyl; wherein A 23 , A 24 , A 25 and A 26 are independently of each other H; C 6 - C 18 aryl; C 6 -Ci 8 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl, or C 1 - C 18 alkyl which is interrupted by -0-; or A 25 and A 26 together form a five or six membered ring,
  • a 27 and A 28 are independently of each other H; C 6 -C 18 aryl; C 6 -C 18 aryl which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 -C 18 alkyl, or C 1 -C 18 alkyl which is interrupted by -0-, A 29 is H; C 6 -C 18 aryl; C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, or C 1 -C 18 alkoxy; C 1 - C 18 alkyl; or C 1 -C 18 alkyl which is interrupted by -O-,
  • a 30 and A 31 are independently of each other C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl, and A 32 is C 1 -C 18 alkyl, C 6 -C 18 aryl, or C 6 -C 18 aryl, which is substituted by C 1 -C 18 alkyl.
  • At least two adjacent substituents form an aromatic or aliphatic fused ring system means two adjacent substituents can form an aromatic ring, such as a phenyl or naphthyl ring, an aliphatic ring, such as a cyclohexyl ring, or a heterocyclic ring, such as a pyridine or pyrrole ring, wherein two or more of such rings can form a fused ring system with the group to which they are bonded.
  • R 1 , A 1 and A 2 are as defined above and X 10 is halogen such as chlorine, bromine or iodine, preferably bromine or iodine.
  • R 1 , X 10 , A 4 and A 7 are as defined above and R is C 1 -C 18 alkyl, in particular C 1 -C 4 alkyl, aryl, in particular phenyl, or aralkyl, in particular benzyl, which can be substituted one to three times with C 1 -C 8 alkyl, C 1 -C 8 alkoxy, or halogen.
  • R is C 1 -C 18 alkyl, in particular C 1 -C 4 alkyl, aryl, in particular phenyl, or aralkyl, in particular benzyl, which can be substituted one to three times with C 1 -C 8 alkyl, C 1 -C 8 alkoxy, or halogen.
  • Compounds of formula be prepared according or in analogy to the method described in US-B-4,778,899.
  • the compound of formula III is synthesized according, or in analogy described to the method disclosed in Synlett 15 (2003) 2389-2391.
  • halogen means fluorine, chlorine, bromine and iodine.
  • C 1 -C 25 alkyl is typically linear or branched - where possible - methyl, ethyl, n-propyl, isopropyl, n-butyl, sec-butyl, isobutyl, tert.-butyl, n-pentyl, 2-pentyl, 3-pentyl, 2,2-dimethylpropyl, n- hexyl, n-heptyl, n-octyl, 1 ,1 ,3,3-tetramethyl butyl and 2-ethylhexyl, n-nonyl, decyl, undecyl, dodecyl, tetradecyl, pentadecyl, hexadecyl, heptadecyl, octadecyl, eicosyl, heneicosyl, docosyl, tetracosyl or pentacosyl, preferably
  • haloalkyl, haloalkenyl and haloalkynyl mean groups given by partially or wholly substituting the above-mentioned alkyl group, alkenyl group and alkynyl group with halogen, such as trifluoromethyl etc.
  • aldehyde group, ketone group, ester group, carbamoyl group and amino group include those substituted by an alkyl group, a cycloalkyl group, an aryl group, an aralkyl group or a heterocyclic group, wherein the alkyl group, the cycloalkyl group, the aryl group, the aralkyl group and the heterocyclic group may be unsubstituted or substituted.
  • silica group means a group of formula -SiR 62 R 63 R 64 , wherein R 62 , R 63 and R 64 are independently of each other a C 1 -C 8 alkyl group, in particular a C 1 -C 4 alkyl group, a C 6 -C 24 aryl group or a C 7 -Ci 2 aralkylgroup, such as a trimethylsilyl group.
  • siloxanyl group means a group of formula -0-SiR 62 R 63 R 64 , wherein R 62 , R 63 and R 64 are as defined above, such as a trimethylsiloxanyl group.
  • C 1 -C 8 alkoxy examples are methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec.-butoxy, isobutoxy, tert.-butoxy, n-pentoxy, 2-pentoxy, 3-pentoxy, 2,2-dimethylpropoxy, n-hexoxy, n- heptoxy, n-octoxy, 1,1 ,3,3-tetramethylbutoxy and 2-ethylhexoxy, preferably C 1 -C 4 alkoxy such as typically methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, sec.-butoxy, isobutoxy, tert.-butoxy.
  • alkylthio group means the same groups as the alkoxy groups, except that the oxygen atom of ether linkage is replaced by a sulfur atom.
  • aryl group is typically C 6 -C 24 aryl, such as phenyl, indenyl, azulenyl, naphthyl, biphenyl, terphenylyl or quadphenylyl, as-indacenyl, s-indacenyl, acenaphthylenyl, phenanthryl, fluoranthenyl, triphenlenyl, chrysenyl, naphthacen, picenyl, perylenyl, pentaphenyl, hexacenyl, pyrenyl, or anthracenyl, preferably phenyl, 1 -naphthyl, 2-naphthyl,
  • C 6 -C 18 aryl examples include phenyl, 1 -naphthyl, 2-naphthyl, 3- or 4-biphenyl, 9-phenanthryl, 2- or 9-fluorenyl, which may be unsubstituted or substituted.
  • aralkyl group is typically C 7 -C 24 aralkyl, such as benzyl, 2-benzyl-2-propyl, ⁇ - phenyl-ethyl, ⁇ , ⁇ -dimethylbenzyl, ⁇ -phenyl-butyl, ⁇ , ⁇ -dimethyl- ⁇ -phenyl-butyl, ⁇ -phenyl- dodecyl, ⁇ -phenyl-octadecyl, ⁇ -phenyl-eicosyl or ⁇ -phenyl-docosyl, preferably C 7 -C 18 aralkyl such as benzyl, 2-benzyl-2-propyl, ⁇ -phenyl-ethyl, ⁇ , ⁇ -dimethylbenzyl, ⁇ -phenyl-butyl, ⁇ , ⁇ -dimethyl- ⁇ -phenyl-butyl, ⁇ -phenyl-dodecyl or ⁇ -phenyl-ocyl
  • aryl ether group is typically a C 6-24 aryloxy group, that is to say O-C 6-24 aryl, such as, for example, phenoxy or 4-methoxyphenyl.
  • aryl thioether group is typically a C 6-24 arylthio group, that is to say S-C & ⁇ aryl, such as, for example, phenylthio or 4-methoxyphenylthio.
  • carbamoyl group is typically a Ci.i 8 carbamoyl radical, preferably Ci -8 carbamoyl radical, which may be unsubstituted or substituted, such as, for example, carbamoyl, methylcarbamoyl, ethylcarbamoyl, n-butylcarbamoyl, tert- butylcarbamoyl, dimethylcarbamoyloxy, morpholinocarbamoyl or pyrrolidinocarbamoyl.
  • cycloalkyl group is typically C 5 -Ci 2 cycloalkyl, such as cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl, preferably cyclopentyl, cyclohexyl, cycloheptyl, or cyclooctyl, which may be unsubstituted or substituted.
  • cycloalkenyl group means an unsaturated alicyclic hydrocarbon group containing one or more double bonds, such as cyclopentenyl, cyclopentadienyl, cyclohexenyl and the like, which may be unsubstituted or substituted.
  • the cycloalkyl group in particular a cyclohexyl group, can be condensed one or two times by phenyl which can be substituted one to three times with C 1 -C 4 -alkyl, halogen and cyano. Examples of such condensed
  • R 51 , R 52 , R 53 , R 54 , R 55 and R 56 are independently of each other C 1 -C 8 -alkyl, C 1 -C 8 - alkoxy, halogen and cyano, in particular hydrogen.
  • a group comprising a five-membered heterocyclic ring, containing one to three heteroatoms selected from the group of nitrogen, oxygen and sulfur means a single five- membered heterocyclic ring, such as thienyl, furyl, furfuryl, 2H-pyranyl, pyrrolyl, imidazolyl, or pyrazolyl, or a five-membered heterocyclic ring which is part of a fused ring system, which is formed by the five-membered heterocyclic ring with aryl, heteroaryl and/or cycloalkyl groups, which can optionally be substituted. Examples of such groups are contained in the list of groups for A 1 and A 2 as well as in the definition of heteroaryl or heterocyclic groups.
  • a group comprising a six-membered heterocyclic ring, containing one to three heteroatoms selected from the group of nitrogen, oxygen and sulfur means a single six- membered heterocyclic ring, such as pyridyl, triazinyl, pyrimidinyl, pyrazinyl, pyridazinyl, or a six-membered heterocyclic ring which is part of a fused ring system, which is formed by the six-membered heterocyclic ring with aryl, heteroaryl and/or cycloalkyl groups, which can optionally be substituted. Examples of such groups are contained in the list of groups for A 1 and A 2 as well as in the definition of heteroaryl or heterocyclic group.
  • heteroaryl or heterocyclic group is a ring with five to seven ring atoms, wherein nitrogen, oxygen or sulfur are the possible hetero atoms, and is typically an unsaturated heterocyclic radical with five to 18 atoms having at least six conjugated ⁇ -electrons such as thienyl, benzo[b]thienyl, dibenzo[b,d]thienyl, thianthrenyl, furyl, furfuryl, 21-l-pyranyl, benzofuranyl, isobenzofuranyl, dibenzofuranyl, phenoxythienyl, pyrrolyl, imidazolyl, pyrazolyl, pyridyl, bipyridyl, triazinyl, pyrimidinyl, pyrazinyl, pyridazinyl, indolizinyl, isoindolyl, indolyl, indazolyl, purinyl, quinoliziny
  • aryl and “alkyl” in alkylamino groups, dialkylamino groups, alkylarylamino groups, arylamino groups and diar ⁇ lgroups are typically C 1 -C 25 aI kyl and C 6 -C 24 aryl, respectively.
  • the above-mentioned groups can be substituted by a C 1 -C 8 alkyl, a hydroxyl group, a mercapto group, C 1 -C 8 alkoxy, C 1 -C 8 alkylthio, halogen, halo-C 1 -C 8 alkyl, a cyano group, an aldehyde group, a ketone group, a carboxyl group, an ester group, a carbamoyl group, an amino group, a nitro group, a silyl group or a siloxanyl group.
  • the present invention relates further to an electroluminescent device having the fluorescent compounds, T-3 to T-10, T-12, T-13, and T-14 to T-17, or the compositions according to the present invention between an anode and a cathode and emitting light by the action of electrical energy.
  • an anode/a hole transporting layer/an electron transporting layer/a cathode in which the compounds or compositions of the present invention are used either as positive-hole transport compound or composition, which is exploited to form the light emitting and hole transporting layers, or as electron transport compounds or compositions, which can be exploited to form the light-emitting and electron transporting layers,
  • an anode/a hole transporting layer/a light-emitting layer/an electron transporting layer/a cathode in which the compounds or compositions form the light-emitting layer regardless of whether they exhibit positive-hole or electron transport properties in this constitution
  • an anode/a hole injection layer /a hole transporting layer/a light-emitting layer/an electron transporting layer/a cathode in which the compounds or compositions form the light-emitting layer regardless of whether they exhibit positive-hole or electron transport properties in this constitution
  • an anode/a hole injection layer /a hole transporting layer/a light-emitting layer/an electron transporting layer/a cathode in which the compounds or compositions form the light-emitting layer regardless of whether they exhibit positive-hole or electron transport properties in this constitution
  • an anode/a hole injection layer /a hole transporting layer/a light-emitting layer/an electron transporting layer/a cathode in which the compounds or compositions form the light-emitting layer regardless of whether they exhibit
  • an anode/a hole injection layer/a hole transporting layer/a light-emitting layer/ a hole- blocking layer /an electron transporting layer/a cathode (v) an anode/a light-emitting layer/an electron transporting layer/a cathode,
  • the compounds and compositions of the present invention can, in principal be used for any organic layer, such as, for example, hole transporting layer, light emitting layer, or electron transporting layer, but are preferably used as the light emitting material in the light emitting layer.
  • the present invention relates to compositions comprising a guest chromophore and a host chromophore, wherein the absorption spectrum of the guest chromophore overlaps with the fluorescence emission spectrum of the host chromophore, wherein the host chromophore is a diketopyrrolopyrrole having a photoluminescence emission peak at 350 to 500 nm, preferably 400 to 470 nm, most preferred 420 to 450 nm, wherein the host and/or the guest chromophore is a compound of formula I, II, or III.
  • compositions comprise a host chromophore of formula I, II, or III or a guest chromophore of formula I, II, or III; or a host chromophore of formula I, II, or III and a guest chromophore of formula I, II, or III.
  • the compounds of formula I, II, or III can be used with other known fluorescent compounds as host or guest compounds, for example: Host:
  • the weight ratio of the host chromophore to the guest chromophore is in general 50:50 to 99.99:0.01 , preferably 90:10 to 99.99:0.01, more preferably 95:5 to 99.9:0.1, most preferred 98:2 to 99.9:0.1.
  • Thin film type electroluminescent devices usually consist essentially of a pair of electrodes and at least one charge transporting layer in between.
  • a hole transporting layer (next to the anode) and an electron transporting layer (next to the cathode) are present.
  • Either one of them contains - depending on its properties as hole-transporting or electron-transporting material - an inorganic or organic fluorescence substance as light-emitting material. It is also common, that a light-emitting material is used as an additional layer between the hole-transporting and the electron-transporting layer.
  • a hole injection layer can be constructed between an anode and a hole transporting layer and/or a positive hole inhibiting layer can be constructed between a light emitting layer and an electron transporting layer to maximise hole and electron population in the light emitting layer, reaching large efficiency in charge recombination and intensive light emission.
  • the devices can be prepared in several ways. Usually, vacuum evaporation is used for the preparation.
  • the organic layers are laminated in the above order on a commercially available indium-tin-oxide ("ITO") glass substrate held at room temperature, which works as the anode in the above constitutions.
  • ITO indium-tin-oxide
  • the membrane thickness is preferably in the range of 1 to 10,000 nm, more preferably 1 to 5,000 nm, more preferably 1 to 1 ,000 nm, more preferably 1 to 500 nm.
  • the cathode metal such as a Mg/Ag alloy, a binary Li-Al or LiF-AI system with an thickness in the range of 50-200 nm is laminated on the top of the organic layers.
  • the vacuum during the deposition is preferably less than 0.1333 Pa (1x 10 ⁇ 3 Torr), more preferably less than 1.333x 10 ⁇ 3 Pa (1x 10 ⁇ 5 Torr), more preferably less than 1.333x 10 "4 Pa (1x 10 "6 Torr).
  • anode materials which possess high work function such as metals like gold, silver, copper, aluminum, indium, iron, zinc, tin, chromium, titanium, vanadium, cobalt, nickel, lead, manganese, tungsten and the like, metallic alloys such as magnesium/copper, magnesium/silver, magnesium/aluminum, aluminum/indium and the like, semiconductors such as Si, Ge, GaAs and the like, metallic oxides such as indium-tin-oxide ("ITO"), ZnO and the like, metallic compounds such as CuI and the like, and furthermore, electroconducting polymers such polyacetylene, polyaniline, polythiophene, polypyrrole, polyparaphenylene and the like, preferably ITO, most preferably ITO on glass as substrate can be used.
  • metallic alloys such as magnesium/copper, magnesium/silver, magnesium/aluminum, aluminum/indium and the like, semiconductors such as Si, Ge, GaAs and the like, metallic oxides
  • metals, metallic alloys, metallic oxides and metallic compounds can be transformed into electrodes, for example, by means of the sputtering method.
  • the electrode can be formed also by the vacuum deposition method.
  • the electrode can be formed, furthermore, by the chemical plating method (see for example, Handbook of Electrochemistry, pp 383-387, Mazuren, 1985).
  • an electrode can be made by forming it into a film by means of anodic oxidation polymerization method onto a substrate which is previously provided with an electroconducting coating.
  • the thickness of an electrode to be formed on a substrate is not limited to a particular value, but, when the substrate is used as a light emitting plane, the thickness of the electrode is preferably within the range of from 1 nm to 300 nm, more preferably, within the range of from 5 to 200 nm so as to ensure transparency.
  • ITO is used on a substrate having an ITO film thickness in the range of from 10 nm (100 A) to 1 ⁇ (10000 A), preferably from 20 nm (200 A) to 500 nm (5000 A).
  • the sheet resistance of the ITO film is chosen in the range of not more than 100 ⁇ /cm 2 , preferably not more than 50 ⁇ /cm 2 .
  • Such anodes are commercially available from Japanese manufacturers, such as Geomatech Co. Ltd., Sanyo Vacuum Co. Ltd., Nippon Sheet Glass Co. Ltd.
  • an electronconducting or electrically insulating material can be used as substrate either an electronconducting or electrically insulating material.
  • a light emitting layer or a positive hole transporting layer is directly formed thereupon, while in case of using an electrically insulating substrate, an electrode is firstly formed thereupon and then a light emitting layer or a positive hole transporting layer is superposed.
  • the substrate may be either transparent, semi-transparent or opaque. However, in case of using a substrate as an indicating plane, the substrate must be transparent or semi- transparent.
  • Transparent electrically insulating substrates are, for example, inorganic compounds such as glass, quartz and the like, organic polymeric compounds such as polyethylene, polypropylene, polymethylmethacrylate, polyacrylonitrile, polyester, polycarbonate, polyvinylchloride, polyvinylalcohol, polyvinylacetate and the like.
  • inorganic compounds such as glass, quartz and the like
  • organic polymeric compounds such as polyethylene, polypropylene, polymethylmethacrylate, polyacrylonitrile, polyester, polycarbonate, polyvinylchloride, polyvinylalcohol, polyvinylacetate and the like.
  • semi-transparent electrically insulating substrates examples include inorganic compounds such as alumina, YSZ (yttrium stabilized zirconia) and the like, organic polymeric compounds such as polyethylene, polypropylene, polystyrene, epoxy resins and the like. Each of these substrates can be transformed into a semi-transparent electroconducting substrate by providing it with an electrode according to one of the abovementioned methods.
  • opaque electroconducting substrates are metals such as aluminum, indium, iron, nickel, zinc, tin, chromium, titanium, copper, silver, gold, platinum and the like, various elctroplated metals, metallic alloys such as bronze, stainless steel and the like, semiconductors such as Si, Ge, GaAs, and the like, electroconducting polymers such as polyaniline, polythiophene, polypyrrole, polyacetylene, polyparaphenylene and the like.
  • a substrate can be obtained by forming one of the above listed substrate materials to a desired dimension. It is preferred that the substrate has a smooth surface. Even, if it has a rough surface, it will not cause any problem for practical use, provided that it has round unevenness having a curvature of not less than 20 ⁇ m. As for the thickness of the substrate, there is no restriction as far as it ensures sufficient mechanical strength.
  • cathode materials which possess low work function such as alkali metals, earth alkaline metals, group 13 elements, silver, and copper as well as alloys or mixtures thereof such as sodium, lithium, potassium, calcium, lithium fluoride (LiF), sodium-potassium alloy, magnesium, magnesium-silver alloy, magnesium-copper alloy, magnesium-aluminum alloy, magnesium-indium alloy, aluminum, aluminum-aluminum oxide alloy, aluminum-lithium alloy, indium, calcium, and materials exemplified in EP-A 499,011 such as electroconducting polymers e.g. polypyrrole, polythiophene, polyaniline, polyacetylene etc., preferably Mg/Ag alloys, LiF-AI or Li-Al compositions can be used.
  • electroconducting polymers e.g. polypyrrole, polythiophene, polyaniline, polyacetylene etc., preferably Mg/Ag alloys, LiF-AI or Li-Al compositions can
  • a magnesium-silver alloy or a mixture of magnesium and silver, or a lithium-aluminum alloy, lithium fluoride-aluminum alloy or a mixture of lithium and aluminum can be used in a film thickness in the range of from 10 nm (100 A) to 1 ⁇ m (10000 A), preferably from 20 nm (200 A) to 500 nm (5000 A).
  • Such cathodes can be deposited on the foregoing electron transporting layer by known vacuum deposition techniques described above.
  • a light-emitting layer can be used between the hole transporting layer and the electron transporting layer.
  • the light-emitting layer is prepared by forming a thin film on the hole transporting layer.
  • the organic EL device of the present invention may comprise an inorganic compound layer between at least one of the electrodes and the above organic thin layer.
  • the inorganic compound used for the inorganic compound layer include various types of oxides, nitrides and oxide nitrides such as alkali metal oxides, alkaline earth metal oxides, rare earth oxides, alkali metal halides, alkaline earth metal halides, rare earth halides, SiO x , AIO x , SiN x , SiON, AION, GeO x , LiO x , LiON, TiO x , TiON, TaO x , TaON, TaN x and C.
  • SiO x , AIO x , SiN x , SiON, AION, GeO x and C are preferable, since a suitable interface layer of injection is formed.
  • the vacuum deposition method As methods for forming said thin film, there are, for example, the vacuum deposition method, the spin-coating method, the casting method, the Langmuir-Blodgett ("LB") method and the like.
  • the vacuum deposition method, the spin-coating method and the casting method are particularly preferred in view of ease of operation and cost.
  • the conditions under which the vacuum deposition is carried out are usually strongly dependent on the properties, shape and crystalline state of the compound(s). However, optimum conditions are usually as follows: temperature of the heating boat: 100 to 400 0 C; substrate temperature: -100 to 350 0 C; pressure: 1.33x10 4 Pa (1x10 2 Torr) to 1.33x10 "4 Pa (1x10 6 Torr) and deposition rate: 1 pm to 6 nm/sec.
  • the thickness of the light emitting layer is one of the factors determining its light emission properties. For example, if a light emitting layer is not sufficiently thick, a short circuit can occur quite easily between two electrodes sandwiching said light emitting layer, and therefore, no EL emission is obtained. On the other hand, if the light emitting layer is excessively thick, a large potential drop occurs inside the light emitting layer because of its high electrical resistance, so that the threshold voltage for EL emission increases. Accordingly, the thickness of the organic light emitting layer is limited to the range of from 5 nm to 5 ⁇ m, preferably to the range of from 10 nm to 500 nm.
  • the coating can be carried out using a solution prepared by dissolving the composition in a concentration of from 0.0001 to 90% by weight in an appropriate organic solvent such as benzene, toluene, xylene, tetrahydrofurane, methyltetrahydrofurane, N,N-dimethylformamide, dichloromethane, dimethylsulfoxide and the like. If the concentration exceeds 90% by weight, the solution usually is so viscous that it no longer permits forming a smooth and homogenous film. On the other hand, if the concentration is less than 0.0001 % by weight, the efficiency of forming a film is too low to be economical. Accordingly, a preferred concentration of the composition is within the range of from 0.01 to 80% by weight.
  • any polymer binder may be used, provided that it is soluble in the solvent in which the composition is dissolved.
  • polymer binders are polycarbonate, polyvinylalcohol, polymethacrylate, polymethylmethacrylate, polyester, polyvinylacetate, epoxy resin and the like.
  • the fluidity of the solution is usually so low that it is impossible to form a light emitting layer excellent in homogeneity.
  • the preferred ratio of the polymer binder to the composition is chosen within the range of from 10:1 to 1 :50 by weight, and the solid content composed of both components in the solution is preferably within the range of from 0.01 to 80% by weight, and more preferably, within the range of 0.1 to 60% by weight.
  • organic hole transporting compounds such as polyvinyl carbazole
  • Q 1 and Q 2 each represent a hydrogen atom or a methyl group
  • T and T 1 stand for an organic radical; a hydrazone based compound
  • R x , R y and R z stand for an organic radical, and the like can be used.
  • Compounds to be used as a positive hole transporting material are not restricted to the above listed compounds. Any compound having a property of transporting positive holes can be used as a positive hole transporting material such as triazole derivatives, oxadiazole derivatives, imidazole derivatives, polyarylalkane derivatives, pyrazoline derivative, pyrazolone derivatives, phenylene diamine derivatives, arylamine derivatives, amino substituted chalcone derivatives, oxazole derivatives, stilbenylanthracene derivatives, fluorenone derivatives, hydrazone derivatives, stilbene derivatives, copolymers of aniline derivatives, PEDOT (poly(3,4-ethylenedioxy-thiophene)) or PEDOT-PSS (poly(3,4- ethylenedioxy-thiophene)-poly(styrenesulfonate)) and the derivatives thereof, electro- conductive oligomers, particularly thiophene oligomers, porphy
  • aromatic tertiary amine compounds such as N,N,N',N'-tetraphenyl-4,4'- diaminobiphenyl, N,N'-diphenyl-N,N'-bis(3-methylphenyl)- 4,4'-diaminobiphenyl (TPD), 2,2'- bis(di-p-torylaminophenyl)propane, 1 ,1'-bis(4-di-torylaminophenyl)-4-phenylcyclohexane, bis(4-dimethylamino-2-methylphenyl)phenylmethane, bis(4-di-p-tolylaminophenyl)phenyl- methane, N,N'-diphenyl-N,N'-di(4-methoxyphenyl)-4,4'-diaminobiphenyl, N, N 1 N', N'- tetraphenyl-4,4'-di
  • a positive hole transporting layer can be formed by preparing an organic film containing at least one positive hole transporting material on the anode.
  • the positive hole transporting layer can be formed by the vacuum deposition method, the spin-coating method, the casting method, ink jet printing method, the LB method and the like. Of these methods, the vacuum deposition method, the spin-coating method and the casting method are particularly preferred in view of ease and cost.
  • the conditions for deposition may be chosen in the same manner as described for the formation of a light emitting layer (see above). If it is desired to form a positive hole transporting layer comprising more than one positive hole transporting material, the coevaporation method can be employed using the desired compounds. In the case of forming a positive hole transporting layer by the spin-coating method or the casting method, the layer can be formed under the conditions described for the formation of the light emitting layer (see above).
  • a smoother and more homogeneous positive hole transporting layer can be formed by using a solution containing a binder and at least one positive hole transporting material.
  • the coating using such a solution can be performed in the same manner as described for the light emitting layer.
  • Any polymer binder may be used, provided that it is soluble in the solvent in which the at least one positive hole transporting material is dissolved. Examples of appropriate polymer binders and of appropriate and preferred concentrations are given above when describing the formation of a light emitting layer.
  • the thickness of the positive hole transporting layer is preferably chosen in the range of from 0.5 to 1000 nm, preferably from 1 to 100 nm, more preferably from 2 to 50 nm.
  • hole injection materials known organic hole transporting compounds such as metal-free phthalocyanine (H 2 Pc), copper-phthalocyanine (Cu-Pc) and their derivatives as described, for example, in JP64-7635 can be used.
  • H 2 Pc metal-free phthalocyanine
  • Cu-Pc copper-phthalocyanine
  • some of the aromatic amines defined as hole transporting materials above, which have a lower ionisation potential than the hole transporting layer, can be used.
  • a hole injection layer can be formed by preparing an organic film containing at least one hole injection material between the anode layer and the hole transporting layer.
  • the hole injection layer can be formed by the vacuum deposition method, the spin-coating method, the casting method, the LB method and the like.
  • the thickness of the layer is preferably from 5 nm to 5 ⁇ m, and more preferably from 10 nm to 100 nm.
  • the electron transporting materials should have a high electron injection efficiency (from the cathode) and a high electron mobility.
  • the following materials can be exemplified for electron transporting materials: tris( ⁇ -hydroxyquinolinato)-aluminum(lll) and its derivatives, bis(10- hydroxybenzo[h]quinolinolato)ber ⁇ llium(ll) and its derivatives, oxadiazole derivatives, such as 2-(4-biphenyl)-5-(4-tert.-butylphenyl)-1,3,4-oxadiazole and its dimer systems, such as 1,3- bis(4-tert.-butylphenyl-1 ,3,4)oxadiazolyl)biphenylene and 1 ,3-bis(4-tert.-butylphenyl-1 ,3,4- oxadiazolyl)phenylene, dioxazole derivatives, triazole derivatives, coumarine derivatives, imidazopyridine derivative
  • hetero-cyclic compounds such as, benzimidazole derivatives, benzoxazole derivatives, thiadiazole derivative, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives, oligo- pyridine derivatives, e.g. bipyridine derivatives and terpyridine derivatives, naphthylidine derivatives, indole derivatives and naphthalimide derivatives; silole derivatives; and phosphineoxide derivatives.
  • hetero-cyclic compounds such as, benzimidazole derivatives, benzoxazole derivatives, thiadiazole derivative, pyrazine derivatives, quinoxaline derivatives, quinoline derivatives, benzoquinoline derivatives, oligo- pyridine derivatives, e.g. bipyridine derivatives and terpyridine derivatives, naphthylidine derivatives, indole derivatives and naphthalimide derivatives; silole derivatives; and
  • the reducing dopant is a material that can reduce the electron transporting material.
  • alkaline metals e.g. Na, K, Rb and Cs
  • alkali earth metals e.g. Ca, Sr and Ba.
  • An electron transporting layer can be formed by preparing an organic film containing at least one electron transporting material on the hole transporting layer or on the light-emitting layer.
  • the electron transporting layer can be formed by the vacuum deposition method, the spin- coating method, the casting method, the LB method and the like.
  • the positive hole inhibiting materials for a positive hole inhibiting layer have high electron injection/transporting efficiency from the electron transporting layer to the light emission layer and also have higher ionisation potential than the light emitting layer to prevent the flowing out of positive holes from the light emitting layer to avoid a drop in luminescence efficiency.
  • the positive hole inhibiting material known materials, such as BaIq, TAZ and phenanthroline derivatives, e.g. bathocuproine (BCP), can be used:
  • the positive hole inhibiting layer can be formed by preparing an organic film containing at least one positive hole inhibiting material between the electron transporting layer and the light-emitting layer.
  • the positive hole inhibiting layer can be formed by the vacuum deposition method, the spin-coating method, the casting method, ink jet printing method, the LB method and the like.
  • the thickness of the layer preferably is chosen within the range of from 5 nm to 2 ⁇ m, and more preferably, within the range of from 10 nm to 100 nm.
  • a smoother and more homogeneous electron transporting layer can be formed by using a solution containing a binder and at least one electron transporting material.
  • the thickness of an electron transporting layer is preferably chosen in the range of from 0.5 to 1000 nm, preferably from 1 to 100 nm, more preferably from 2 to 50 nm.
  • the property of charge injection can be improved by adding an electron-accepting compound to the hole injection layer and/or the hole transporting layer and an electron-donating material to the electron transporting layer.
  • the host chromphore is a compound having a photoluminescence emission peak at 350 to 500 nm, preferably 400 to 470 nm, most preferred 420 to 450 nm.
  • the light-emitting compositions have a fluorescence emission maximum in the range of from 400 to 500, preferably from 420 to 480, more preferred from 440 to 460 nm. Further, the inventive compounds preferably exhibit an absorption maximum in the range of 300 to 460 nm.
  • the light-emitting compositions usually exhibit a fluorescence quantum yield ("FQY") in the range of from 1 > FQY > 0.3 (measured in aerated toluene or DMF). Further, in general, the inventive compositions exhibit a molar absorption coefficient in the range of from 5000 to 100000.
  • FQY fluorescence quantum yield
  • Another embodiment of the present invention relates to a method of coloring high molecular weight organic materials (having a molecular weight usually in the range of from 10 3 to 10 7 g/mol; comprising biopolymers, and plastic materials, including fibres) by incorporating therein the inventive compounds or compositions by methods known in the art.
  • high molecular weight organic materials having a molecular weight usually in the range of from 10 3 to 10 7 g/mol; comprising biopolymers, and plastic materials, including fibres
  • inventive compounds and compositions can be used, as described for the DPP compounds of formula T in EP-A-1087005, for the preparation of inks, for printing inks in printing processes, for flexographic printing, screen printing, packaging printing, security ink printing, intaglio printing or offset printing, for pre-press stages and for textile printing, for office, home applications or graphics applications, such as for paper goods, for example, for ballpoint pens, felt tips, fiber tips, card, wood, (wood) stains, metal, inking pads or inks for impact printing processes (with impact-pressure ink ribbons), for the preparation of colorants, for coating materials, for industrial or commercial use, for textile decoration and industrial marking, for roller coatings or powder coatings or for automotive finishes, for high-solids (low-solvent), water-containing or metallic coating materials or for pigmented formulations for aqueous paints, for the preparation of pigmented plastics for coatings, fibers, platters or mold carriers, for the preparation of non-impact-printing material for digital printing, for the thermal
  • Another preferred embodiment concerns the use of the inventive compounds and compositions for color changing media.
  • inventive compounds or compositions are useful for EL materials for the above category (i) and, in addition, for the above mention technique (ii).
  • inventive compounds or compositions are useful for EL materials for the above category (iii) as an element of white luminescent in combination of other compensatory electroluminescence to construct white luminescent.
  • Particularly preferred high molecular weight organic materials are, for example, cellulose ethers and esters, e.g. ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate, natural resins or synthetic resins (polymerization or condensation resins) such as aminoplasts, in particular urea/formaldehyde and melamine/formaldehyde resins, alkyd resins, phenolic plastics, polycarbonates, polyolefins, polystyrene, polyvinyl chloride, polyamides, poly- urethanes, polyester, ABS, ASA, polyphenylene oxides, vulcanized rubber, casein, silicone and silicone resins as well as their possible mixtures with one another.
  • cellulose ethers and esters e.g. ethylcellulose, nitrocellulose, cellulose acetate and cellulose butyrate
  • natural resins or synthetic resins polymerization or condensation resins
  • aminoplasts in particular urea/form
  • organic materials in dissolved form as film formers, for example boiled linseed oil, nitrocellulose, alkyd resins, phenolic resins, melamine/formaldehyde and urea/formaldehyde resins as well as acrylic resins.
  • film formers for example boiled linseed oil, nitrocellulose, alkyd resins, phenolic resins, melamine/formaldehyde and urea/formaldehyde resins as well as acrylic resins.
  • Said high molecular weight organic materials may be obtained singly or in admixture, for example in the form of granules, plastic materials, melts or in the form of solutions, in particular for the preparation of spinning solutions, paint systems, coating materials, inks or printing inks.
  • inventive compounds and compositions are used for the mass coloration of polyvinyl chloride, polyamides and, especially, polyolefins such as polyethylene and polypropylene as well as for the preparation of paint systems, including powder coatings, inks, printing inks, color filters and coating colors.
  • Illustrative examples of preferred binders for paint systems are alkyd/melamine resin paints, acryl/melamine resin paints, cellulose acetate/cellulose butyrate paints and two-pack system lacquers based on acrylic resins which are crosslinkable with polyisocyanate.
  • another embodiment of the present invention relates to a composition
  • a composition comprising (a) 0.01 to 50, preferably 0.01 to 5, particularly preferred 0.01 to 2% by weight, based on the total weight of the coloured high molecular organic material, of a fluorescent compound or of a composition according to the present invention, and (b) 99.99 to 50, preferably 99.99 to 95, particularly preferred 99.99 to 98% by weight, based on the total weight of the coloured high molecular organic material, of a high molecular organic material, and (c) optionally, customary additives such as rheology improvers, dispersants, fillers, paint auxiliaries, siccatives, plasticizers, UV-stabilizers, and/or additional pigments or corresponding precursors in effective amounts, such as e.g. from 0 to 50% by weight, based on the total weight of (a) and (b).
  • customary additives such as rheology improvers, dispersants, fillers, paint auxiliaries, siccatives,
  • the inventive fluorescent DPP compounds of formula I or the inventive compositions may advantageously be used in admixture with fillers, transparent and opaque white, colored and/or black pigments as well as customary luster pigments in the desired amount.
  • the corresponding high molecular weight organic materials, such as binders, synthetic resin dispersions etc. and the inventive compounds or compositions are usually dispersed or dissolved together, if desired together with customary additives such as dispersants, fillers, paint auxiliaries, siccatives, plasticizers and/or additional pigments or pigment precursors, in a common solvent or mixture of solvents. This can be achieved by dispersing or dissolving the individual components by themselves, or also several components together, and only then bringing all components together, or by adding everything together at once.
  • the present invention relates also to a method of coloring a high molecular weight organic material by incorporating therein the inventive compounds or compositions by known methods in the art.
  • a further embodiment of the present invention relates to a method of using the inventive compounds or compositions for the preparation of dispersions and the corresponding dispersions, and paint systems, coating materials, color filters, inks and printing inks comprising the inventive compositions.
  • a particularly preferred embodiment relates to the use of the inventive compounds or compositions for the preparation of fluorescent tracers for e.g. leak detection of fluids such as lubricants, cooling systems etc., as well as to fluorescent tracers or lubricants comprising the inventive compositions.
  • the inventive compounds or compositions are mixed with the high molecular weight organic materials using roll mills, mixing apparatus or grinding apparatus.
  • the pigmented material is subsequently brought into the desired final form by conventional processes, such as calandering, compression molding, extrusion, spreading, casting or injection molding.
  • the high molecular weight organic materials and the inventive compounds or compositions alone or together with additives, such as fillers, other pigments, siccatives or plasticizers, are generally dissolved or dispersed in a common organic solvent or solvent mixture.
  • additives such as fillers, other pigments, siccatives or plasticizers
  • the present invention additionally relates to inks comprising a coloristically effective amount of the pigment dispersion of the inventive compositions.
  • the weight ratio of the pigment dispersion to the ink in general is chosen in the range of from 0.001 to 75% by weight, preferably from 0.01 to 50% by weight, based on the overall weight of the ink.
  • the color filters can be coated for example using inks, especially printing inks, which can comprise pigment dispersions comprising the inventive compositions or can be prepared, for example, by mixing a pigment dispersion comprising an inventive composition with chemically, thermally or photolytically structurable high molecular weight organic material (so-called resist).
  • the subsequent preparation can be carried out, for example, in analogy to EP-A 654 711 by application to a substrate, such as a LCD (liquid crystal display), subsequent photostructuring and development.
  • pigment dispersions comprising an inventive compound or composition which possess non-aqueous solvents or dispersion media for polymers.
  • the present invention relates, moreover, to toners comprising a pigment dispersion containing an inventive compound or composition or a high molecular weight organic material pigmented with an inventive composition in a coloristically effective amount.
  • the present invention additionally relates to colorants, colored plastics, polymeric ink particles, or non-impact-printing material comprising an inventive composition, preferably in the form of a dispersion, or a high molecular weight organic material pigmented with an inventive composition in a coloristically effective amount.
  • a coloristically effective amount of the pigment dispersion according to this invention comprising an inventive composition denotes in general from 0.0001 to 99.99% by weight, preferably from 0.001 to 50% by weight and, with particular preference, from 0.01 to 50% by weight, based on the overall weight of the material pigmented therewith.
  • inventive compositions can be applied to colour polyamides, because they do not decompose during the incorporation into the polyamides. Further, they exhibit an exceptionally good lightfastness, a superior heat stability, especially in plastics.
  • the organic EL device of the present invention has significant industrial values since it can be adapted for a flat panel display of an on-wall television set, a flat light-emitting device, a light source for a copying machine or a printer, a light source for a liquid crystal display or counter, a display signboard and a signal light.
  • the compounds and compositions of the present invention can be used in the fields of an organic EL device, an electrophotographic photoreceptor, a photoelectric converter, a solar cell, an image sensor, and the like.

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Life Sciences & Earth Sciences (AREA)
  • Veterinary Medicine (AREA)
  • Animal Behavior & Ethology (AREA)
  • General Health & Medical Sciences (AREA)
  • Public Health (AREA)
  • Epidemiology (AREA)
  • Birds (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Dermatology (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

La présente invention concerne des composés fluorescents répondant à la formule (I), (II) ou (III), leur procédé de préparation et leur utilisation pour la préparation d’encres, de colorants, de plastiques pigmentés pour des revêtements, de matériaux d’impression sans choc, de filtres de couleur, de produits de beauté, de particules d'encre polymère, de toners, en tant que traceurs fluorescents, dans des milieux changeant de couleur, des lasers à colorant et des dispositifs électro-luminescents. Un dispositif luminescent comprenant un composé selon la présente invention est performant en termes d’efficacité de l'utilisation de l'énergie électrique et de luminance.
PCT/EP2006/063527 2005-07-05 2006-06-26 Dicétopyrrolopyrroles et dérivés fluorescents WO2007003520A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
EP05106066 2005-07-05
EP05106066.3 2005-07-05

Publications (1)

Publication Number Publication Date
WO2007003520A1 true WO2007003520A1 (fr) 2007-01-11

Family

ID=35478914

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2006/063527 WO2007003520A1 (fr) 2005-07-05 2006-06-26 Dicétopyrrolopyrroles et dérivés fluorescents

Country Status (1)

Country Link
WO (1) WO2007003520A1 (fr)

Cited By (17)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011119446A1 (fr) * 2010-03-20 2011-09-29 Polyera Corporation Composés semi-conducteurs à pyrrolo[3,2-b]pyrrole et dispositifs qui incorporent lesdits composés
WO2012079675A3 (fr) * 2010-12-17 2012-08-09 Merck Patent Gmbh Polymères conjugués
WO2012123060A1 (fr) 2011-03-11 2012-09-20 Merck Patent Gmbh Polymères conjugués
WO2012130365A1 (fr) 2011-03-25 2012-10-04 Merck Patent Gmbh Pyrrolo[3,2-b]pyrrole-2,5-diones et leur utilisation en tant que semi-conducteurs organiques
WO2012175530A1 (fr) 2011-06-22 2012-12-27 Basf Se Oligomères de dicétopyrrolopyrrole destinés à être utilisés dans des dispositifs semi-conducteurs organiques
WO2013013765A1 (fr) 2011-07-27 2013-01-31 Merck Patent Gmbh Petites molécules et leur utilisation en tant que semi-conducteurs organiques
WO2013030325A1 (fr) 2011-09-02 2013-03-07 Basf Se Oligomères de dicétopyrrolopyrrole et compositions comprenant des oligomères de dicétopyrrolopyrrole
WO2014070029A1 (fr) * 2012-11-05 2014-05-08 Instytut Chemii Organicznej Polskiej Akademii Nauk Nouveaux hétérocycles fortement fluorescents et procédé pour leur synthèse
JP2014514413A (ja) * 2011-04-28 2014-06-19 ビーエーエスエフ ソシエタス・ヨーロピア チエノチオフェン−２，５−ジオンオリゴマー及びポリマーに基づく半導体材料
WO2014156718A1 (fr) * 2013-03-28 2014-10-02 富士フイルム株式会社 Transducteur photoélectrique, élément d'imagerie, capteur optique et procédé d'utilisation d'un transducteur photoélectrique
US9029695B2 (en) 2013-02-24 2015-05-12 Raynergy Tek Inc. Heteroaromatic semiconducting polymers
WO2016193243A1 (fr) 2015-06-03 2016-12-08 Udc Ireland Limited Dispositifs oled très efficaces à temps de déclin très courts
WO2016171465A3 (fr) * 2015-04-20 2016-12-22 주식회사 엘지화학 Composé hétérocyclique et cellule solaire organique le comprenant
EP3220435A4 (fr) * 2014-11-14 2017-11-15 Fujifilm Corporation Élément semi-conducteur organique et composé
CN107502344A (zh) * 2017-09-12 2017-12-22 中南大学 基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒及制备和应用
US10347851B2 (en) 2013-12-20 2019-07-09 Udc Ireland Limited Highly efficient OLED devices with very short decay times
WO2021033656A1 (fr) * 2019-08-21 2021-02-25 富士フイルム株式会社 Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image

Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5354869A (en) * 1988-07-29 1994-10-11 Riedel-De Haen Aktiengesellschaft 3,6-bis-(2'-methoxyphenyl)-2,5-dihydro-2,5-dimethyl-pyrrolo-(3,4-c)-pyrrole-1,4-dione compound
WO2003064558A1 (fr) * 2002-02-01 2003-08-07 Ciba Specialty Chemicals Holdings Inc. Compositions fluorescentes comprenant des dicetopyrrolopyrroles

Patent Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US5354869A (en) * 1988-07-29 1994-10-11 Riedel-De Haen Aktiengesellschaft 3,6-bis-(2'-methoxyphenyl)-2,5-dihydro-2,5-dimethyl-pyrrolo-(3,4-c)-pyrrole-1,4-dione compound
WO2003064558A1 (fr) * 2002-02-01 2003-08-07 Ciba Specialty Chemicals Holdings Inc. Compositions fluorescentes comprenant des dicetopyrrolopyrroles

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
CHAN W-K ET AL: "RATIONAL DESIGNS OF MULTIFUNCTIONAL POLYMERS", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, AMERICAN CHEMICAL SOCIETY, WASHINGTON, DC, US, vol. 115, no. 25, 1993, pages 11735 - 11743, XP000652156, ISSN: 0002-7863 *

Cited By (44)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2011119446A1 (fr) * 2010-03-20 2011-09-29 Polyera Corporation Composés semi-conducteurs à pyrrolo[3,2-b]pyrrole et dispositifs qui incorporent lesdits composés
JP2013525514A (ja) * 2010-03-20 2013-06-20 ポリエラ コーポレイション ピロロ［３，２−ｂ］ピロール半導体化合物およびそれを組み込んだデバイス
US8598448B2 (en) 2010-03-20 2013-12-03 Polyera Corporation Pyrrolo[3,2-B]pyrrole semiconducting compounds and devices incorporating same
JP2014507488A (ja) * 2010-12-17 2014-03-27 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツング 共役ポリマー
WO2012079675A3 (fr) * 2010-12-17 2012-08-09 Merck Patent Gmbh Polymères conjugués
US9048433B2 (en) 2010-12-17 2015-06-02 Merck Patent Gmbh Conjugated polymers
CN103261204B (zh) * 2010-12-17 2016-08-10 默克专利股份有限公司 共轭聚合物
CN103261204A (zh) * 2010-12-17 2013-08-21 默克专利股份有限公司 共轭聚合物
GB2501199A (en) * 2010-12-17 2013-10-16 Merck Patent Gmbh Conjugated polymers
KR20130132545A (ko) * 2010-12-17 2013-12-04 메르크 파텐트 게엠베하 공액 중합체
WO2012123060A1 (fr) 2011-03-11 2012-09-20 Merck Patent Gmbh Polymères conjugués
WO2012130365A1 (fr) 2011-03-25 2012-10-04 Merck Patent Gmbh Pyrrolo[3,2-b]pyrrole-2,5-diones et leur utilisation en tant que semi-conducteurs organiques
JP2014514413A (ja) * 2011-04-28 2014-06-19 ビーエーエスエフ ソシエタス・ヨーロピア チエノチオフェン−２，５−ジオンオリゴマー及びポリマーに基づく半導体材料
JP2014528908A (ja) * 2011-06-22 2014-10-30 ビーエーエスエフ ソシエタス・ヨーロピアＢａｓｆ Ｓｅ 有機半導体素子内で使用するためのジケトピロロピロールオリゴマー
WO2012175530A1 (fr) 2011-06-22 2012-12-27 Basf Se Oligomères de dicétopyrrolopyrrole destinés à être utilisés dans des dispositifs semi-conducteurs organiques
CN103703007A (zh) * 2011-07-27 2014-04-02 默克专利股份有限公司 小分子及其作为有机半导体的用途
WO2013013765A1 (fr) 2011-07-27 2013-01-31 Merck Patent Gmbh Petites molécules et leur utilisation en tant que semi-conducteurs organiques
JP2014529343A (ja) * 2011-07-27 2014-11-06 メルク パテント ゲゼルシャフト ミット ベシュレンクテル ハフツングＭｅｒｃｋ Ｐａｔｅｎｔ Ｇｅｓｅｌｌｓｃｈａｆｔ ｍｉｔ ｂｅｓｃｈｒａｅｎｋｔｅｒ Ｈａｆｔｕｎｇ 小分子および有機半導体としてのそれらの使用
WO2013030325A1 (fr) 2011-09-02 2013-03-07 Basf Se Oligomères de dicétopyrrolopyrrole et compositions comprenant des oligomères de dicétopyrrolopyrrole
US9209412B2 (en) 2011-09-02 2015-12-08 Basf Se Diketopyrrolopyrrole oligomers and compositions, comprising diketopyrrolopyrrole oligomers
CN104870447A (zh) * 2012-11-05 2015-08-26 波兰科学院有机化学研究所 强荧光性杂环类和它们的合成方法
US9988385B2 (en) 2012-11-05 2018-06-05 Instytut Chemii Organicznej Polskiej Akademii Nauk Strongly fluorescent heterocycles and a method for their synthesis
WO2014070029A1 (fr) * 2012-11-05 2014-05-08 Instytut Chemii Organicznej Polskiej Akademii Nauk Nouveaux hétérocycles fortement fluorescents et procédé pour leur synthèse
US9029695B2 (en) 2013-02-24 2015-05-12 Raynergy Tek Inc. Heteroaromatic semiconducting polymers
WO2014156718A1 (fr) * 2013-03-28 2014-10-02 富士フイルム株式会社 Transducteur photoélectrique, élément d'imagerie, capteur optique et procédé d'utilisation d'un transducteur photoélectrique
JP2015062213A (ja) * 2013-03-28 2015-04-02 富士フイルム株式会社 光電変換素子、撮像素子、光センサ、光電変換素子の使用方法
US10559763B2 (en) 2013-03-28 2020-02-11 Fujifilm Corporation Photoelectric conversion element, imaging device, optical sensor, and method of using photoelectric conversion element
US10177320B2 (en) 2013-03-28 2019-01-08 Fujifilm Corporation Photoelectric conversion element, imaging device, optical sensor, and method of using photoelectric conversion element
US11765967B2 (en) 2013-12-20 2023-09-19 Udc Ireland Limited Highly efficient OLED devices with very short decay times
EP3916822A1 (fr) 2013-12-20 2021-12-01 UDC Ireland Limited Dispositifs oled hautement efficaces avec de très courts temps de détérioration
US11075346B2 (en) 2013-12-20 2021-07-27 Udc Ireland Limited Highly efficient OLED devices with very short decay times
US10347851B2 (en) 2013-12-20 2019-07-09 Udc Ireland Limited Highly efficient OLED devices with very short decay times
EP3220435A4 (fr) * 2014-11-14 2017-11-15 Fujifilm Corporation Élément semi-conducteur organique et composé
US10217942B2 (en) 2014-11-14 2019-02-26 Fujifilm Corporation Organic semiconductor element, manufacturing method thereof, compound, composition for forming organic semiconductor film, and organic semiconductor film
WO2016171465A3 (fr) * 2015-04-20 2016-12-22 주식회사 엘지화학 Composé hétérocyclique et cellule solaire organique le comprenant
US10906922B2 (en) 2015-04-20 2021-02-02 Lg Chem, Ltd. Heterocyclic compound and organic solar cell comprising same
KR101785200B1 (ko) 2015-04-20 2017-10-17 주식회사 엘지화학 헤테로환 화합물 및 이를 포함하는 유기 태양 전지
EP4060757A1 (fr) 2015-06-03 2022-09-21 UDC Ireland Limited Dispositifs delo hautement efficaces avec de très courts temps de déclin
WO2016193243A1 (fr) 2015-06-03 2016-12-08 Udc Ireland Limited Dispositifs oled très efficaces à temps de déclin très courts
CN107502344B (zh) * 2017-09-12 2019-07-19 中南大学 基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒及制备和应用
CN107502344A (zh) * 2017-09-12 2017-12-22 中南大学 基于吡咯并吡咯二酮类化合物和四苯乙烯类化合物的多功能有机荧光纳米颗粒及制备和应用
WO2021033656A1 (fr) * 2019-08-21 2021-02-25 富士フイルム株式会社 Composition colorante, film, filtre optique, élément d'imagerie à semi-conducteurs et dispositif d'affichage d'image
JPWO2021033656A1 (fr) * 2019-08-21 2021-02-25
JP7290731B2 (ja) 2019-08-21 2023-06-13 富士フイルム株式会社 着色組成物、膜、光学フィルタ、固体撮像素子及び画像表示装置

Similar Documents

Publication Publication Date Title
WO2007003520A1 (fr) Dicétopyrrolopyrroles et dérivés fluorescents
JP5523402B2 (ja) 蛍光ジケトピロロピロール
EP1817392B1 (fr) Dicetopyrrolopyrroles fluorescents
US20050008892A1 (en) Fluorescent compositions comprising diketopyrrolopyrroles
US7749404B2 (en) Fluorescent diketopyrrolopyrroles
WO2006003090A1 (fr) Quinacridones fluorescentes
EP1087006B1 (fr) Dispositifs électroluminescents comprenant des dicétopyrrolopyrroles
US20080217580A1 (en) Organic Luminescent Element
KR20040086312A (ko) 디케토피롤로피롤을 포함하는 형광 조성물

Legal Events

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

Ref country code: DE

WWW Wipo information: withdrawn in national office

Country of ref document: DE

122 Ep: pct application non-entry in european phase

Ref document number: 06763870

Country of ref document: EP

Kind code of ref document: A1