EP2111435A1 - Anions/cations polymères - Google Patents

Anions/cations polymères

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Publication number
EP2111435A1
EP2111435A1 EP08707112A EP08707112A EP2111435A1 EP 2111435 A1 EP2111435 A1 EP 2111435A1 EP 08707112 A EP08707112 A EP 08707112A EP 08707112 A EP08707112 A EP 08707112A EP 2111435 A1 EP2111435 A1 EP 2111435A1
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EP
European Patent Office
Prior art keywords
light
emitting device
emitter
polymer
charged
Prior art date
Legal status (The legal status 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 status listed.)
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Application number
EP08707112A
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German (de)
English (en)
Inventor
Hartmut Yersin
Uwe Monkowius
Dominik Pentlehner
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Merck Patent GmbH
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Merck Patent GmbH
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Publication of EP2111435A1 publication Critical patent/EP2111435A1/fr
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    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
    • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
    • H10K85/1135—Polyethylene dioxythiophene [PEDOT]; Derivatives thereof
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/321—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3]
    • H10K85/324—Metal complexes comprising a group IIIA element, e.g. Tris (8-hydroxyquinoline) gallium [Gaq3] comprising aluminium, e.g. Alq3
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/342—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising iridium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/344—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising ruthenium
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
    • H10K85/622—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing four rings, e.g. pyrene
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1425—Non-condensed systems
    • 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
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission

Definitions

  • the present invention relates to light emitting devices, and more particularly to organic light emitting devices (OLEDs).
  • OLEDs organic light emitting devices
  • the invention relates to emitter materials in which charged metal complexes are bound to a polymer by electrostatic interactions.
  • OLEDs organic light emitting diodes
  • the first OLEDs were developed in 1987 (Tang, CW et al., Appl. Phys. Let. 51, 913 (1987)).
  • the functioning of OLEDs is based on a multilayer structure comprising an emitter layer, a hole line layer and an electron conductor layer.
  • the layers consist predominantly of organic substrates, which can be made very thin and flexible.
  • OLED devices can be produced over a large area as lighting elements or screens, but also in the form of smaller displays.
  • the various organic layers are applied to a carrier material.
  • a carrier material For this purpose, essentially two different techniques are used. In vacuum evaporation, molecules are vapor-deposited in vacuo. In a wet-chemical process, the layers are applied from a solution, for example by spin coating, inkjet printing, doctor blading or screen printing.
  • OLEDs have been described, for example, in H. Yersin, Top. Curr. Chem. 2004, 241.
  • An overview of the function of OLEDs can also be found in C. Adachi et al., Appl. Phys. Lett. 2001, 78, 1622; XH Yang et al., Appl. Phys. Lett., 2004, 84, 2476; J. Shinar, "Organic light-emitting devices - A survey", AIP-Press, Springer, New York, 2004; W. Sotoyama et al., Appl. Phys. Lett., 2005, 86, 153505, S. Okada et al , Dalton Trans.
  • triplet or phosphorescent emitters have been the focus of research. It was found that with phosphorescent emitters a much larger electroluminescent quantum yield can be achieved than with so-called singlet emitters. Whereas in singlet emitters (purely organic compounds) only a transition from the excited singlet state to the singlet state leads to an emission of light, higher electroluminescent quantum yields are possible for organometallic complexes, since they undergo transition from the excited triplet state Light is emitted.
  • Triplet emitters are described, for example, in WO 2004/017042 A2 (Thompson), WO 2004/016711 A1 (Thompson), WO 03/095587 (Tsuboyama), US 2003/0205707 (Chi-Ming Che), US 2002/0179885 (Chi-Ming Che), US 2003/186080 A1 (J. Kamatani), DE 103 50 606 A1 (pestle), DE 103 38 550 (Bold), DE 103 58 665 A1 (Lennartz), WO 2007/118671 (Yersin). Higher electroluminescent quantum yields can also be achieved using phosphorescent lanthanide complexes.
  • the known emitter materials have various disadvantages. For example, the low thermal stability and the chemical stability to water and oxygen are problematic. In addition, many emitter materials have too short a lifetime for use in high-end electronic applications. There is also a need for improvement with regard to good synthetic accessibility and production-related reproducibility.
  • Metal complexes can not be applied by vacuum evaporation.
  • a wet-chemical application prepares the crystallization / salt formation
  • the object of the present invention was to make charged emitters and, in particular, charged phosphorescent or triplet-emitter metal complexes usable for use in OLED devices.
  • Immobilization of the emitters can be achieved by attachment to a polymer.
  • the strategy of covalently attaching complexes to polymers is described, for example, in PK Ng et al., Chem. Eur. J. 2001, 7, 4358; X. Chen et al., J. Am. Chem. Soc. 2003, 125, 636 and in J. Hjelm et al., Inorg. Chem. 2005, 44, 1073.
  • the synthetic accessibility of phosphorescent polymers with covalently bound triplet emitters has hitherto only been achieved by very expensive methods - A -
  • the materials can only be obtained in multi-step synthesis processes and often in unsatisfactory yields.
  • the subject of the present invention is a light-emitting device comprising
  • an emitter layer disposed between and in direct or indirect contact with the anode and the cathode and comprising at least one charged emitter and an oppositely charged polymeric matrix interacting by electrostatic forces.
  • the charged emitter is preferably a metal complex, which is preferably a phosphorescent emitter or a triplet emitter.
  • the emitter layer comprises one or more same or different charged emitters which are bonded by electrostatic interaction to an oppositely charged polymeric matrix.
  • the term "emitter” or “emitter metal complex” encompasses both individual compounds and a plurality of compounds as well as charged, emitting clusters or metal complex aggregates and is not to be understood as meaning that in the emitter layer only a single type of emitter-metal complexes is included.
  • the emitter comprises an anionic metal complex and the matrix comprises a cationic polymer.
  • the emitter comprises a cationic metal complex and the matrix comprises an anionic polymer.
  • the emitter layer may include one or more types of charged emitters and one or more charged polymeric matrix materials.
  • the emitter layer comprises at least two or more different charged emitters.
  • the emitters may have the same or different charges.
  • the emitters may be bonded to the same polymeric matrix or to different polymeric matrix materials or different units of the same polymeric matrix.
  • the emitter layer may include both anionic emitters bonded to a cationic polymer and cationic emitters bonded to an anionic polymer.
  • Cationic metal complexes suitable as emitters for use in the present invention have, for example, the formula (I): wherein:
  • M is a metal ion, which is preferably selected from Mo, Ru, Rh, Pd, Ag, W, Re 1 Os, Ir, Pt, Cu and Au;
  • M can also be selected from the group of lanthanides;
  • Each L CH is independently a chelating ligand, for example a bidentate or polydentate ligand;
  • Each L is independently a monodentate ligand;
  • x is an integer from 1 to 3, especially 1 or 2;
  • y is an integer from 0 to 6, especially from 1 to 4, eg 2;
  • n is an integer from 1 to 4, in particular 1 or 2.
  • Examples of chelating ligands L are CH C ° E and E n E, E n E n E and E 0 CTE wherein:
  • E is selected from elements of the fifth main group such as N, P 1 or a carbene-carbon C-C
  • R in the above formulas for the chelating ligand L CH can each independently be hydrogen, halogen, in particular chloride or bromide, pseudohalogen, in particular thiocyanate, cyanate or cyanide, alkyl, aryl, heteroaryl, alkenyl.
  • CO carbon monoxide
  • NR 3 amines
  • imine CR
  • PR 3 phosphines
  • AsR 3 arsines
  • RCN nitriles
  • RCN isonitrile
  • ROR ether
  • disulfide RSR
  • ReR diselenide
  • ReR diselenide
  • L can also be an anionic ligand, for example from the group of halides (F 1 Cr, Br, I), pseudohalides (CN “ , OCN “ , SCN), alkylic anions (eg CH 3 " ), arylic anions (eg Ph “ ), Alcoholates (RO “ ), Thiolates (RS), Hydroxide (OH).
  • halides F 1 Cr, Br, I
  • pseudohalides CN “ , OCN “ , SCN
  • alkylic anions eg CH 3 "
  • arylic anions eg Ph "
  • Alcoholates RO "
  • RS Thiolates
  • Two monodentate ligands L may also be bridged to a bidentate chelating ligand L n L.
  • the advantage of using bidentate ligands over monodentate ligands lies in the higher stability of the resulting complexes. Examples of bidentate
  • Preferred bidentate ligands are L n L
  • Each R is independently hydrogen, halogen, especially chloride or bromide, pseudohalogen, especially thiocyanate, cyanate or cyanide, alkyl, aryl, heteroaryl, alkenyl, each directly or via oxygen (-OR), nitrogen (-NR 2 ) or silicon (-SiR 3 ) may be bonded and which may optionally be substituted with substituents such as halogens, lower alkyl groups and other donor and acceptor groups. Two or more groups R may also be linked together, eg to form annelated ring systems.
  • Preferred cationic emitters are also metal complexes containing a cryptand ligand, eg.
  • Ln lathanoids Preferred example is the blue-emitting ⁇ Ce [2.2.2] cryptand ⁇ 3+
  • Anionic metal complexes suitable as emitters for use in the present invention have, for example, the formula (II): wherein:
  • M is a metal ion, which is preferably selected from Mo, Ru, Rh, Pd, Ag 1 W, Re, Os, Ir, Pt, Cu and Au; M can also be chosen from the group of lanthanides;
  • Each L CH is independently a chelating ligand, for example a bidentate ligand;
  • Each L is independently a monodentate ligand; x is an integer from 1 to 3, especially 1 or 2; y is an integer from 0 to 6, especially from 1 to 4, e.g. 2 is; n is an integer from 1 to 4, in particular 1 or 2.
  • CO carbon monoxide
  • NR 3 amines
  • phosphenes PR 3
  • arsines AsR 3
  • RCN nitriles
  • RCN isonitrile
  • ROR ether
  • disulfide RRR
  • ReR diselenide
  • ReR diselenide
  • L can also be an anionic ligand, for example from the group of halides (F “ , Cr, Br, I), pseudohalides (CN ' , OCN-, SCN), alkylic anions (eg CH 3 ), arylic anions (eg Ph '). ), Alcoholates (RO) 1 Thiolates (RS “ ), Hydroxide (OH).
  • L is preferably X, where
  • Each X is independently a single negatively charged, monodentate ligand, eg CL, Br, I 1 CN, SCN and / or OCN.
  • the chelate ligand LC H is preferably a bidentate ligand C n E in which:
  • E is selected from elements of the fifth main group such as N, As, P, or a carbene-carbon Ccarben;
  • Y is O 1 S or NR
  • Each R is independently hydrogen, halogen, especially chloride or bromide, pseudohalogen, especially thiocyanate, cyanate or cyanide, alky, aryl, heteroaryl, alkenyl, each directly or via oxygen (-OR), nitrogen (-NR 2 ) or silicon (-SiR 3 ) may be bonded and which may optionally be substituted with substituents such as halogens, lower alkyl groups (Ci-C 6 ) and other donor and acceptor groups. Two or more groups R may also be linked together, eg to form annelated ring systems.
  • emitter-loaded organic emitter molecules are used.
  • these are fluorescent organic molecules, and most preferably are charged laser dyes.
  • Preferred compounds are, for example, coumarins, rhodamines, fluoresceins, quinolines, pyrenes, cyanines, triarylmethanes, diarylmethanes, azo dyes, polyenes, polymethines, carbonyl dyes, porphyrins, corrins, phthalocyanines, xanthenes, anthraquinones and borates, which are monosubstituted or polysubstituted or unsubstituted can.
  • Suitable substituents include alkyl, for example Ci-C 2 o-alkyl, in particular Ci-C6 alkyl, halogen, especially F, Cl 1 Br or J, SO 3 -, SO 4 ", COO", SO 2 CI, CF 3, OH, NH 2, NHR, NR 2, wherein R in particular Ci-C 6 alkyl or C 5 -C represents 0 aryl, alkoxy, in particular Ci-C 20 alkoxy, N (CH 2 COO) 2, keto , NH-CO-NH-NH 2 .
  • An advantage of using charged organic emitters, especially fluorescence emitters, is that virtually all colors can be realized with these molecules, from the blue to the red.
  • Particularly preferred suitable anionic fluorescent organic emitters are shown below.
  • Anionic organic emitters can also be obtained by using acids.
  • Suitable acids are, for example
  • Deprotonation of the acids leads to an anionic form.
  • carboxylic acids sulfonic acids or other compounds with acidic hydrogen atoms anions are generated by deprotonation.
  • Cationic fluorescent organic emitters suitable according to the invention can preferably be selected from the groups coumarins, rhodamines, fluoresceins, quinolines, pyrenes, cyanines, triarylmethanes, diarylmethanes, azo dyes, polyenes, polymethines, carbonyl dyes, porphyrins, corrins, phthalocyanines, xanthenes, anthraquinones and borates which may be unsubstituted or monosubstituted or polysubstituted.
  • Suitable substituents include alkyl, for example Ci-C 2 o-alkyl, in particular Ci-C6 alkyl, halogen, especially F, Cl, Br or J, SO 3 ', SO 4', COO ', SO 2 CI, CF 3, OH, NH 2, NHR, NR 2, wherein R in particular Ci-C 6 - alkyl or C 5 -C represents 0 aryl, alkoxy, in particular Ci-C 20 alkoxy, N (CH 2 COO) 2, keto , NH-CO-NH-NH 2 .
  • alkyl for example Ci-C 2 o-alkyl, in particular Ci-C6 alkyl, halogen, especially F, Cl, Br or J, SO 3 ', SO 4', COO ', SO 2 CI, CF 3, OH, NH 2, NHR, NR 2, wherein R in particular Ci-C 6 - alkyl or C 5 -C represents 0 aryl, alkoxy, in particular Ci-C
  • P (OH) O 3 " aryl, in particular C 5 -C 10 -aryl, COOR, OCO-R, where R is in particular alkyl, for example C 1 -C 20 -aryl, which is saturated or mono- or polyunsaturated, CH 2 CO 2 ' , CH 2 CH (CO 2 H) 2 or CN and NR 3 + , wherein R is in particular Ci-C 6 alkyl or Cs-Cio-aryl, NC 4 H 4 O 2 , NC 4 H 2 O. 2 or SCN.
  • An essential element of the present invention is the use of a polymeric matrix containing charged groups. Since the charged groups are constituents of polymer molecules, they can not migrate even when voltage is applied in an electric field. According to the invention, the emitter molecules can then be bound to the charged groups via electrostatic forces, as a result of which charged emitter molecules, even when external voltages are applied, are immobilized.
  • the charges contained in the polymeric matrix may be located at side chains and / or in the polymer backbone.
  • oppositely charged emitter complexes are coordinated to substantially all of the charges contained in the polymeric matrix. It is particularly advantageous if the charge of the polymer matrix is completely compensated by oppositely charged emitter complexes and substantially no additional ionic constituents are contained in the emitter layer.
  • the emitter layer preferably has no small, easily mobile ions.
  • the charges of the polymeric matrix are only partially compensated by oppositely charged emitter complexes.
  • the small ions still contained migrate in the applied electric field to the oppositely charged electrode until an equilibrium is established.
  • the corresponding device is then based on the same functionality as light emitting electrochemical cells (LECs or LEECs).
  • the charged polymeric matrix of the present invention is obtainable by any method known in the art, such as by polymerization, polycondensation, polyaddition or the like Coupling reactions such as Suzuki or Heck clutch.
  • the term "polymeric matrix” or “polymer” is used collectively for all types of polymer production.
  • the charge (s) can be introduced into the polymeric matrix after polymer preparation. However, it is also possible to use already charged monomeric building blocks for the synthesis of the charged matrix according to the invention. Moreover, in one embodiment of the invention it is provided that the charge of the matrix is generated only by combination with an emitter. For example, a polymeric matrix having acidic groups can be deprotonated by reaction with a basic emitter and thus negatively charged.
  • the charged polymeric matrix is composed of at least two or more different monomeric units.
  • the advantage of a copolymer is that the properties of the polymer can be modified according to the specific requirements. By selecting particular monomer building blocks, e.g. the degree of cross-linking can be regulated and good film-forming, glass transition temperature, hole and
  • the polymeric matrix is composed of charged and uncharged units.
  • a polymer composed only partially of units having charged groups has the advantage that substantially complete occupancy of the matrix with oppositely charged emitters can be more easily achieved.
  • the presence of additional charge carriers can be avoided, and it is particularly possible to produce an emitter layer which does not have small, easily mobile ions.
  • Such a matrix is obtainable, for example, by subsequently introducing charges into a polymer at some points while leaving others uncharged.
  • a polymeric organic nitrogen compound can be partially quaternized by the amount of quaternizing agent used is not chosen stoichiometrically but correspondingly lower.
  • acid groups in a polymer can be partially deprotonated. It is also possible to use a copolymer of two or more different charged and uncharged monomer building blocks.
  • Suitable negatively charged polymeric matrix materials according to the present invention are polymers which have a deprotonatable group.
  • Examples of negatively charged groups whose charge is reached (formally) by deprotonation are sulfonates, carboxylates, alcoholates, thiolates and mono- and diesters of ortho-phosphoric acid.
  • Examples of anionic (deprotonated) polymers are:
  • n and m are each independently the number of repeating units and in particular a number from 3 to 10 000, preferably from 10 to 1000 and particularly preferably from 20 to 500.
  • the combination of a positively charged emitter material complex and a negatively charged polymeric matrix according to the present invention can be prepared by reacting a basic metal complex such as [(bpy) 3 Ru] 2+ (OH) 2 with an acidic polymer.
  • a neutralization reaction for example, water is formed as a by-product, which can be easily removed by conventional methods.
  • no further interfering impurities are formed, which under certain circumstances would have to be separated off in a purification step. In this way, it is also very easy to adjust the occupancy rate.
  • Another negative charge polymeric matrix of the present invention is a polymer having permanent anionic groups.
  • permanent anionic side groups are tetraorganyl borates. These may, for example, be linked via linker groups L 'as a side chain to a polymer.
  • linker groups L 'as a side chain to a polymer may, for example, be linked via linker groups L 'as a side chain to a polymer.
  • the permanent anionic Groups also be part of a polymer backbone.
  • the linker L ' is preferably an alkyl or aryl group.
  • R is as defined above.
  • the anionic polymeric matrix may be a copolymer of two or more different monomers.
  • the properties of the polymeric matrix can be controlled thereby targeted.
  • polymeric nitrogen compounds such as amines, amides, imines and enamines can be used in which the nitrogen atoms are partially or completely quaternized.
  • the nitrogen may be part of the polymer main chain or in particular a side group.
  • polymerizable primary amines are e.g. commercially available:
  • a positively charged polymeric matrix can be prepared according to the present invention by at least partially quaternizing a polymeric aromatic nitrogen compound with a quaternizing reagent.
  • polymeric quaternary nitrogen compounds examples include:
  • X is selected from the group comprising halogen, e.g. Cl, Br, I,
  • Pseudohalogen eg CN, SCN, OCN 1 tosylate, triflate.
  • R is as defined above.
  • polymeric quaternary nitrogen compounds are:
  • Ternary sulfur compounds such as, for example, can also be used as the cationic polymeric matrix Poly (3 I 3 l, 4 I 4'-benzophenonetetracarboxylic dianhydride-a / f-thionin)
  • quaternizing reagents are alkylating agents of the general formula RX, wherein R represents an alkyl radical such as methyl, ethyl, propyl or butyl and in which X is preferably a good leaving group such as iodide, bromide, tosylate, triflate, etc.
  • RX alkylating agent
  • X is preferably a good leaving group such as iodide, bromide, tosylate, triflate, etc.
  • An example of a particularly suitable quaternizing reagent is MeI.
  • the use of methyl iodide results in an iodide-containing polymer. If necessary, it is possible to exchange iodide with other anions such as Cl " or CN ' .
  • the nitrogen atoms contained in the polymeric nitrogen compound, in particular in the polymeric aromatic nitrogen compound are only partially quaternized.
  • the partial quaternization proceeds as follows:
  • Another example of a partially quaternized polymeric nitrogen compound is:
  • the partial quaternization of a polymeric nitrogen compound and in particular of a polymeric aromatic nitrogen compound has the advantage that the quaternization proceeds statistically and the degree of coverage can be well adjusted. However, coordinating nitrogen atoms remain, which may possibly affect the emission properties of the emitter.
  • each positively charged quaternary ammonium group an emitter molecule is coordinated.
  • the polymeric matrix has, in addition to quaternary aromatic nitrogen compounds, other different monomers, for example non-quaternized aromatic nitrogen compounds or other monomer building blocks. By selecting the other neutral monomers, the properties of the polymeric matrix can be controlled.
  • the copolymerization proceeds, for example, as follows:
  • Another example of a copolymer according to the invention is:
  • Another approach for preparing a positively charged matrix of the invention involves the polymerization of monomers containing quaternary N atoms. Since very clean (monomer) compounds are available as starting compounds, the resulting polymers are also well defined in their composition.
  • the polymerization of monomeric quaternary salts has the advantage that a polymerization directly on a substrate, such as ITO, can be carried out.
  • a polymerization directly on a substrate such as ITO
  • the charged emitter is bonded to an oppositely charged polymeric matrix only via electrostatic interaction.
  • the charged emitter is additionally covalently bonded to a polymer or part of a polymer. Due to the covalent attachment of the emitter is immobilized and further restricted in its movement.
  • the emitter can be bound to side chains of the polymer and / or itself be part of the polymer main chain.
  • the emitter is a charged triplet-emitter metal complex.
  • the charged emitter is bound via electrostatic interaction to an oppositely charged polymeric matrix and additionally by covalent bonding to a second polymer bound.
  • the second polymer is preferably uncharged itself.
  • the polymer is the oppositely charged polymeric matrix.
  • the charged emitter is then electrostatically and covalently attached to the matrix.
  • the emitter layer comprises a polymeric zwitterion which is composed of a charged emitter and an oppositely charged matrix.
  • the emitter may be attached to side chains of a polymer or be part of a polymer backbone.
  • a covalent attachment of an emitter to a polymer numerous possibilities are known in the art, and the present invention should not be limited to a particular possibility of attachment.
  • emitter-metal complexes which have a functional group on at least one ligand can be bonded via one or more ligands to a side chain of a polymer.
  • a metal complex can also be attached via the functionality of a ligand to a monomer, which is subsequently converted into a polymer.
  • an emitter which itself has polymerizable groups for example on one or more ligands of a metal complex
  • polymerize or “polymerization” is used in summary for all types of polymer production.
  • a polymer can be formed according to the present invention, for example by polymerization, polycondensation, polyaddition and / or coupling reactions, for example by Heck or Suzuki coupling.
  • the charged emitter is bonded to a polymer composed of at least two different monomeric units.
  • a copolymer is that the properties of the polymer can be modified as required. By using certain monomer building blocks, for example, a good film formation and Locht. Electron conductivity, etc. can be achieved.
  • the charged metal complex is part of a polymer backbone.
  • an emitter complex which has at least two functionalities on its ligand can be contained as a monomer unit in a polymer chain.
  • a metal complex is combined as a monomer with other monomers and incorporated by polymerization, polycondensation, polyaddition, coupling reactions, metathesis and others in a polymer chain.
  • At least two different charged emitters are used.
  • Each of these emitters can be bonded to an oppositely charged polymeric matrix only via electrostatic interactions, or in addition covalently bonded to a polymer or be part of a polymer according to the above.
  • the emitters may be bound to side chains of a polymer or be part of the polymer main chain, wherein the polymer may be a copolymer.
  • the emission spectrum can be changed depending on their concentrations in the layer.
  • white light can be generated by using two or more triplet emitters.
  • polymer-bound anionic emitters examples include
  • both anions and cations can be immobilized, which can also be achieved by covalent bonding of the emitters to polymers.
  • This is e.g. possible when the emitter on the ligand has a functional group reactive enough to bond to a monomer or polymer.
  • the ligand is called 4- (2-pyridyl) benzaldehyde, which upon reaction with a primary amine (monomer or polymer) forms an imine and thus forms the linkage between emitter and polymer.
  • the first example shows a two vinyl-functionalized iridium complex (L 'represents a linker, e.g., an alkyl group that should be sufficiently long, or groups that have, for example, hole or electron conductor properties) that is polymerized by a metathesis reaction.
  • L ' represents a linker, e.g., an alkyl group that should be sufficiently long, or groups that have, for example, hole or electron conductor properties
  • Advantageous here is the copolymerization with a further divinyl compound in order to be able to better adjust the emitter concentration.
  • An analogous principle is the use of poly-coupling reactions (e.g., Suzuki, Heck, et al.) And other polymerization reactions (polycondensation, addition, etc.). Also possible is the use of polymers or oligomers with end groups which are suitable for further polymerization.
  • the polymer zwitterionic with anionic emitter complex and with the cation in the side chain or as part of the polymer chain.
  • the copolymerization with monomers which carry further functionalities (hole or electron conductivity) is also possible.
  • polymer-bound ligands are commercially available, e.g. Phosphane ligands (3-5) or polymer-bound pyridine (3) are commercially available.
  • the metal center may be part of the cationic polymer chain rather than just attached to a side chain.
  • This type of polymers is generally referred to as coordination polymers.
  • the material again contains a polyanion.
  • this class of compounds differs from the already known from the literature, polymer-bonded emitter complexes containing as counterion always non-polymeric (molecule) anions (eg Cl “ , BF 4 ' , PF 6 " , triflate, etc.).
  • metal-containing precursors can be prepared by adding an at least bifunctional ligand directly to coordination polymers react.
  • the first example shows an iridium complex functionalized with two vinyl groups (L 'represents a linker, eg an alkyl group that should be as long as possible, or groups that have eg hole or electron conductor properties) that is polymerized by a metathesis reaction.
  • L ' represents a linker, eg an alkyl group that should be as long as possible, or groups that have eg hole or electron conductor properties
  • the copolymerization with a further divinyl compound is certainly advantageous here in order to be able to better adjust the emitter concentration.
  • An analogous principle is the use of poly-coupling reactions (eg Suzuki, Heck, etc.) and other polymerization reactions (polycondensation, addition, etc.). Another possibility is the use of polymers or oligomers with end groups which are suitable for further polymerization.
  • the structure of the light-emitting device according to the invention may be that of any known device of the prior art described above.
  • the structure of OLED devices is described in detail, for example, in US2005 / 0260449 A1 and in WO 2005/098988 A1.
  • the device comprises at least one anode, a cathode and an emitter layer.
  • one or both of the electrodes used as the cathode or anode is made transparent, so that the light can be emitted by this electrode.
  • Preferred is as transparent electrode material indium tin oxide (ITO) used.
  • ITO indium tin oxide
  • a transparent anode is used.
  • the other electrode may also be formed of a transparent material, but may also be formed of another material with suitable electron work function, if light is to be emitted only by one of the two electrodes.
  • the second electrode, in particular the cathode consists of a metal with low electron work function and good electrical conductivity, for example of aluminum, or silver, or a Mg / Ag or a Ca / Ag alloy.
  • an emitter layer is arranged. This may be in direct contact with the anode and the cathode, or in indirect contact, where indirect contact means that further layers are included between the cathode or anode and the emitter layer so that the emitter layer and the anode and / or cathode do not touch each other , but are electrically connected to each other via further intermediate layers.
  • a voltage for example a voltage of 3 - 20 V, in particular of 5 - 10 V
  • the cathode for example a conductive metal layer, e.g. from an aluminum cathode negatively charged electrons and migrate towards the positive anode.
  • the organometallic complexes of the formulas (I) or (II) are present as emitter molecules.
  • the migrating charge carriers ie a negatively charged electron and a positively charged hole, recombine, leading to energetically excited states of the emitter molecules.
  • the excited states of the emitter molecules then give off their energy as light emission.
  • the emitter layer takes over functions of the hole or electron conduction layer.
  • the light-emitting device according to the invention also has a CsF intermediate layer between the cathode and the emitter layer or an electron conductor layer.
  • This layer has in particular a thickness of 0.5 nm to 2 nm, preferably of about 1 nm.
  • This intermediate layer mainly causes a reduction of the electron work function.
  • the light-emitting device is applied to a substrate, for example on a glass substrate.
  • An OLED structure for a soluble emitter according to the invention particularly preferably has the structure described below and illustrated in FIG. 2, but comprises at least one, more preferably at least two, and most preferably all of the layers mentioned below.
  • the device is preferably applied to a carrier material, in particular to glass or another solid or flexible transparent material.
  • An anode is applied to the carrier material, for example an indium tin oxide anode (ITO).
  • the layer thickness of the anode is preferably 10 nm to 100 nm, in particular 30 to 50 nm.
  • a hole transport layer (HTL) is applied to the anode and between anode and emitter layer, in particular of a hole conductor material which is water-soluble.
  • a hole conductor material is, for example, PEDOT / PSS (polyethylenedioxythiophene / polystyrenesulfonic acid).
  • the layer thickness of the HTL layer is preferably 10 to 100 nm, in particular 40 to 60 nm.
  • the emitter layer (EML) is applied, which contains an emitter according to the invention.
  • the material may be dissolved in a solvent, for example acetone, dichloromethane or acetonitrile. Thereby, dissolution of the underlying layer (e.g.
  • the emitter material according to the invention contains a metal complex occupancy in a suitable concentration which prevents or severely restricts triplet triplet annihilation. Particularly suitable are concentrations between 3% and 12%.
  • a layer of electron transport layer is preferably applied to the emitter layer, in particular with a layer thickness of 10 to 80 nm, more preferably 30 to 50 nm.
  • a suitable material for the electron transport layer is, for example, Alq 3 , which is vapor-deposited ,
  • a thin intermediate layer is preferably applied which reduces the electron injection barrier and protects the ETL layer.
  • This layer preferably has a thickness of between 0.5 and 2 nm, in particular between 0.5 and 1.0 nm, and preferably consists of CsF or LiF. This layer is usually applied by evaporation.
  • the ETL layer and / or the interlayer may be omitted if the OLED structure is further simplified.
  • a conductive cathode layer is applied, in particular vapor-deposited.
  • the cathode layer is preferably made of a metal, in particular of Al, Ag or Mg / Ag (in particular in the ratio 10: 1).
  • the intermediate layer is preferably very thin, in particular 0.5 to 2 nm, more preferably 0.8 to 1.0 nm thick. Voltages of 3 to 15 V are preferably applied to the device.
  • the entire structure of the light emitting device is preferably encapsulated with a suitable material to substantially prevent the ingress of water or oxygen.
  • Fig. 1 simplified schematic representation of the operation of an OLED
  • FIG. 3 Emission spectra of the polymer films [PAA] n + mCln [(ppy) PtCl 2 ] m from Example 2 at different coverage levels at room temperature.
  • Fig. 4 emission spectra of the polymers of Example 3 with different occupancy levels. The reference also shows the emission of polyacrylic acid doped with [Ru (bpy) 3 ] Cl 2 .
  • PA polyacrylic acid
  • [Ru (bpy) 3 ] CI 2 selected.
  • the precursor used in a first step was the Compound [Ru (bpy) 3 ] (OH) 2 x 2 H 2 O is prepared by shaking an aqueous solution of [Ru (bpy) 3 ] Cl 2 with an aqueous suspension of Ag 2 O in excess in a separating funnel. The excess Ag 2 O was filtered off together with the resulting AgCl and the solvent was removed from the filtrate in vacuo. In order to obtain the desired coverage, the basic complex and the acidic polymer were weighed in the appropriate proportions and stirred in water at room temperature for 12 h.
  • an occupancy rate of approximately 4% is particularly suitable.

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Abstract

La présente invention concerne les dispositifs électroluminescents et notamment les dispositifs électroluminescents organiques (OLED). L'invention concerne plus particulièrement les matériaux émetteurs dans lesquels des complexes métalliques chargés sont liés à un polymère par des interactions électrostatiques.
EP08707112A 2007-01-17 2008-01-17 Anions/cations polymères Withdrawn EP2111435A1 (fr)

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DE102007002420A DE102007002420A1 (de) 2007-01-17 2007-01-17 Polymere Anionen/Kationen
PCT/EP2008/000347 WO2008087031A1 (fr) 2007-01-17 2008-01-17 Anions/cations polymères

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US8766238B2 (en) 2014-07-01
WO2008087031A1 (fr) 2008-07-24
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US20100059740A1 (en) 2010-03-11
DE102007002420A1 (de) 2008-07-24

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