EP1977432A1 - Materiaux electroluminescents et leur utilisation - Google Patents

Materiaux electroluminescents et leur utilisation

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Publication number
EP1977432A1
EP1977432A1 EP07702866A EP07702866A EP1977432A1 EP 1977432 A1 EP1977432 A1 EP 1977432A1 EP 07702866 A EP07702866 A EP 07702866A EP 07702866 A EP07702866 A EP 07702866A EP 1977432 A1 EP1977432 A1 EP 1977432A1
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EP
European Patent Office
Prior art keywords
different
occurrence
units
substituted
aromatic
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.)
Ceased
Application number
EP07702866A
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German (de)
English (en)
Inventor
Junyou Pan
René SCHEURICH
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Merck Patent GmbH
Original Assignee
Merck Patent GmbH
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Publication date
Application filed by Merck Patent GmbH filed Critical Merck Patent GmbH
Publication of EP1977432A1 publication Critical patent/EP1977432A1/fr
Ceased legal-status Critical Current

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    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C08G61/12—Macromolecular compounds containing atoms other than carbon in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D493/00—Heterocyclic compounds containing oxygen atoms as the only ring hetero atoms in the condensed system
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L65/00—Compositions of macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain; Compositions of derivatives of such polymers
    • 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
    • G—PHYSICS
    • G02—OPTICS
    • G02B—OPTICAL ELEMENTS, SYSTEMS OR APPARATUS
    • G02B6/00—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings
    • G02B6/10—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type
    • G02B6/12—Light guides; Structural details of arrangements comprising light guides and other optical elements, e.g. couplings of the optical waveguide type of the integrated circuit kind
    • G02B6/13—Integrated optical circuits characterised by the manufacturing method
    • G02B6/138—Integrated optical circuits characterised by the manufacturing method by using polymerisation
    • 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
    • H10K85/154—Ladder-type polymers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/60—Organic compounds having low molecular weight
    • H10K85/649—Aromatic compounds comprising a hetero atom
    • H10K85/653—Aromatic compounds comprising a hetero atom comprising only oxygen as 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
    • C09K2211/1441—Heterocyclic
    • C09K2211/145—Heterocyclic containing oxygen as the only 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
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only 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
    • C09K2211/1441—Heterocyclic
    • C09K2211/1491—Heterocyclic containing other combinations of heteroatoms
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to electroluminescent materials, that is to say: monomers, polymers, blends and formulations comprising these polymers and the use of the monomers, polymers, blends and formulations according to the invention in electronic and optoelectronic components.
  • full-color display elements full-color displays
  • various classes of materials have already been proposed or developed.
  • poly-fluorene derivatives and also poly-spirobifluorene, poly-dihydrophenanthrene and poly-indenofluorene derivatives are suitable.
  • Polymers containing a combination of two or more of these structural elements have also been proposed.
  • polymers containing poly-para-phenylene (PPP) as a structural element are used.
  • the polymers according to the prior art may show already good properties in use in PLED's. However, despite the progress already made, these polymers do not yet meet the require- changes made to them for high quality applications. In particular, the life of the green and especially the blue-emitting polymers is not sufficient for many applications. The same applies to the efficiency of the red-emitting polymers. Furthermore, with many blue-emitting polymers according to the prior art, the emission color is not yet sufficiently deep blue.
  • OFET 's organic field effect transistors: most of the stable OFET 's today are based on a fast p-channel. It is of the highest interest to have OFET ' s with stable e - channel, as this is a drastic simplification of the architecture of the driving
  • Polymers containing structural elements of formula (1) or (2) are known as materials for use in OLED displays. They are described in WO 03/099901, WO 05/033174 and WO 04/039859.
  • the present invention relates to polymers containing at least 0.5 mol%, preferably at least 5 mol%, more preferably at least 10 mol% and in particular at least 50 mol% units of the formula (3), wherein the symbols and indices used have the following meanings :
  • M is identical or different at each occurrence, an aromatic, heteroaromatic or non-aromatic ring system having 2 to 40 carbon atoms, which is unsubstituted or with one or a plurality of radicals R 1 may be substituted, which may be the same or different at each occurrence,
  • R 1 may be the same or different at each occurrence and as defined below
  • Yi, Y 2 , Y 3 is the same or different at each instance and is a bridge which, with M, spans a cyclic system selected from B (R 1 ),
  • j establishes the linkage to the polymer and may be at each
  • Occurrence may be the same or different and is defined below or is -N-Ar,
  • R 2 is identical or different H, halogen
  • R 3 is the same or different at each occurrence and is a straight-chain, branched or cyclic alkyl or alkoxy group having 1 to 10 C atoms, an aromatic or heteroaromatic ring system having 2 to 24 C atoms, which may be substituted two substituents R 3 also together form a mono- or polycyclic ring system,
  • n, m, p are the same or different 0, 1 or 2 for each occurrence, with the proviso that at least one n or m must be 1 or 2, but preferably with the proviso that not all n, m and p are simultaneously 1 or 2, and
  • q can integer values of 1 to 10 6 , 1 preferably from to
  • An aromatic ring system in the sense of the present invention contains 6 to 40 carbon atoms in the ring system.
  • a heteroaromatic ring system in the sense of the present invention contains 2 to 40 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of the C atoms and heteroatoms gives at least 5.
  • the heteroatoms are preferably selected from Si, N, P 1 O, S and / or Ge, more preferably selected from N, P, O and / or S.
  • An aromatic or heteroaromatic ring system in the context of the present invention is to be understood as a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups are replaced by a short, non-aromatic moiety (less than 10% of the atoms other than H, preferably less than 5% of the atoms other than H), such as z.
  • a C, N or O atom can be interrupted.
  • systems such as 9,9'-spirobifluorene, 9,9-diaryl fluorene, triarylamine, diaryl ethers, etc. are also to be understood as aromatic ring systems in the context of the present invention.
  • a non-aromatic ring system in the sense of the present invention contains 3 to 40, preferably 6 to 40 carbon atoms in the ring system and includes both saturated and partially unsaturated ring systems, which may be unsubstituted or mono- or polysubstituted by radicals R 1 , the may be the same or different at each occurrence and may also contain one or more heteroatoms, preferably Si, N, P, O, S and / or Ge 1 particularly preferably N, P, O and / or S. These may be, for example, cyclohexyl-type or piperidine-type systems, but also cyclooctadiene-type ring systems. Also fused non-aromatic ring systems should be understood by this.
  • a C1 to C40 alkyl group in which individual H atoms or CH 2 groups can be substituted by the aforementioned groups, more preferably the methyl, ethyl, n-propyl, i- Propyl, cyclopropyl, n-butyl, i-butyl, s-butyl, t-butyl, cyclobutyl, 2-methylbutyl, n-pentyl, s-pentyl, cyclopentyl, n-hexyl, cyclohexyl, n-heptyl, cycloheptyl, n- Octyl, cyclooctyl, 2-ethylhexyl, trifluoromethyl, pentafluoroethyl, 2,2,2-trifluoroethyl, ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexyl,
  • a C 1 to C 40 alkoxy group is more preferably understood to mean methoxy, ethoxy, n-propoxy, isopropoxy, n-butoxy, isobutoxy, s-butoxy, t-butoxy or 2-methylbutoxy.
  • C2-C40 aryl or heteroaryl group which may be monovalent or bivalent depending on the use, which may be substituted in each case with the abovementioned radicals R 1 and which may be linked via any position on the aromatic or heteroaromatic
  • aromatic and heteroaromatic ring systems in the context of the present invention in particular biphenyls, terphenyls, fluorene, spirobifluorene, dihydrophenanthrene, tetrahydropyrenes and cis- or trans-indenofluorene understood in addition to the abovementioned aryl and heteroaryl groups.
  • R 1 may be, more preferably for an aryl or heteroaryl group selected from benzene, naphthalene, anthracene, phenanthrene, pyridine, pyrene and thiophene, in particular benzene, which may be substituted in each case with one or two radicals R 1 .
  • R 1 denotes a straight-chain, branched or cyclic alkyl chain having 2 to 15 C atoms, in which one or more non-adjacent carbon atoms are also present.
  • the two radicals R 1 together may also form a further mono- or polycyclic, aromatic or aliphatic ring system.
  • q has integer values of from 1 to 10, preferably from 1 to 6 and particularly preferably from 1 to 4.
  • One aspect of the invention is conjugated polymers. Another aspect of the invention is non-conjugated
  • in yet another aspect of the invention are partially conjugated polymers. Preference is given to conjugated or partially conjugated polymers.
  • a further aspect of the present invention may be branched polymers, which are to be understood as meaning both highly branched and dendrimeric polymer structures.
  • Conjugated polymers in the context of the present invention are polymers which contain in the main chain mainly sp 2 -hybridized carbon atoms, which may also be replaced by corresponding heteroatoms. In the simplest case this means alternating presence of double and single bonds in the main chain. Mainly, of course, suggests that naturally occurring defects that lead to conjugation disruptions do not invalidate the term "conjugated polymer".
  • conjugated if in the main chain, for example arylamine units and / or certain heterocycles (ie conjugation of N, O or S atoms) and / or organometallic complexes (ie conjugation via the metal atom) are ,
  • units such as simple alkyl bridges, (thio) ether, ester, amide or imide linkages are clearly defined as non-conjugated segments.
  • a partially conjugated polymer is meant a polymer in which longer conjugated portions in the main chain are interrupted by non-conjugated portions, or which contains longer conjugated portions in the side chains of a non-conjugated polymer in the main chain.
  • the polymers according to the invention may contain, in addition to units of the formula (3), further structural elements. These include those as disclosed and listed in WO 02/077060 and WO 05/014689.
  • the further structural units can come, for example, from the following classes: Group 1: units which increase the hole injection and / or transport properties of the polymers;
  • Group 2 units which increase the electron injection and / or transport properties of the polymers
  • Group 3 units comprising combinations of Group 1 and Group 2 individual units
  • Group 4 units which change the emission characteristics to the extent that electrophosphorescence is obtained instead of electro-fluorescence;
  • Group 5 units that improve the transition from the singlet to the triplet state
  • Group 6 units which influence the morphology or also the emission color of the resulting polymers
  • Group 7 units which are typically used as backbone.
  • Preferred polymers according to the invention are those in which at least one structural element has charge transport properties, ie. H. contain the units from groups 1 and / or 2.
  • these arylamines and heterocycles lead to a HOMO in the polymer of greater than -5.8 eV (vs. vacuum level), more preferably greater than -5.5 eV.
  • these units in the polymer result in a LUMO of less than -2.7 eV (vs. vacuum level), more preferably less than -3.0 eV.
  • the polymers according to the invention may contain units from group 3 in which structures which increase hole mobility and which increase electron mobility (that is to say units from groups 1 and 2) are bonded directly to one another. Some of these units can serve as emitters and shift the emission color to green, yellow or red. Their use is thus suitable, for example, for the production of other emission colors from originally blue-emitting polymers.
  • Structural units from group 4 are those which can emit light from the triplet state at room temperature with high efficiency, ie exhibit electrophosphorescence instead of electrofluorescence, which frequently results in an increase in energy efficiency.
  • Compounds which contain heavy atoms with an atomic number of more than 36 are suitable for this purpose.
  • compounds containing d- or f-transition metals which satisfy the above condition.
  • Very particular preference is given here to corresponding structural units which contain elements of group 8 to 10 (Ru, Os, Rh, Ir, Pd, Pt) but also lanthanide complexes (for example Eu 3+ ).
  • Structural units for the polymers of the invention come here z.
  • WO 04/026886 are described. Corresponding monomers are described in WO 02/068435 and in DE 10350606 A1. Group 5 structural elements are those which enhance the singlet to triplet state transition and which, when used in support of the Group 4 structural elements, improve the phosphorescence properties of these structural elements. Carbazole and bridged carbazole dimer units, in particular, are suitable for this purpose, as described in WO 04/070772 and WO 04/113468. Also suitable for this purpose are ketones, phosphine oxides, sulfoxides, sulfones, silane derivatives and similar compounds, as described in DE 10349033 A1.
  • Group 6 structural elements which influence the morphology or also the emission color of the polymers are, in addition to those mentioned above, those which have at least one further aromatic or another conjugated structure which does not fall under the abovementioned groups, ie the charge carrier mobility only which are not organometallic complexes or have no influence on the singlet-triplet transition. Such structural elements can influence the morphology, but also the emission color of the resulting polymers. Depending on the unit, they can therefore also be used as emitters. Preference is given to aromatic structures having 6 to 40 carbon atoms or else toluenes, stilbene or bisstyrylarylene derivatives, each of which may be substituted by one or more radicals R 1 .
  • Particularly preferred is the incorporation of 1, 4-phenylene, 1, 4-naphthylene, 1, 4- or 9,10-anthrylene, 2,7- or 3,6-phenanthrylene, 1, 6, 2,7- or 4,9-pyrenylene-, 3,9- or 3,10
  • Group 7 structural elements are units having aromatic structures of from 6 to 40 carbon atoms, which are typically used as the polymer backbone. These are, for example, 4,5-dihydropyrene derivatives, 4,5,9,10-tetrahydropyrene derivatives, fluorene derivatives, 9,9'-spirobifluorene derivatives, phenanthrene derivatives, 9,10-dihydrophenanthrene derivatives, 5,7-dihydrodibenzooxepine derivatives and and trans-indenofluorene derivatives. However, since the proportion of units of the formula (3) is more particularly at least 50 mol%, these structural elements are preferably not used as the main polymer skeleton.
  • Structural units according to formula (3) additionally contain one or more units selected from groups 1 to 7. It may also be preferred if more than one structural unit from a group is present at the same time.
  • the proportion of the units of the formula (3) is preferably at least 5 mol%, particularly preferably at least 10 mol% and in particular at least 50 mol%. This preference applies in particular when the units of formula (3) are the polymer backbone.
  • other proportions may be preferred, for example, a fraction of the order of 0.5 to 20 mol%, if it is the hole conductor or the emitter in an electroluminescent polymer.
  • the preferred proportion may again be different, for example, up to 100 mol%, when it comes to hole- or electron-conducting units.
  • polymers according to the invention which, in addition to structural units of the formula (3), also contain at least one structural unit from the abovementioned groups 1 to 7. Particularly preferred are at least two structural units from different of the above classes. Most preferably, one of these structural units is selected from the group of hole-conducting units, and the other group is an emitting unit, whereby these two functions (hole conduction and emission) can also be taken over by the same unit.
  • Units of the formula (3) are also particularly suitable for the synthesis of white-emitting copolymers. These preferably contain a sufficiently small proportion of green and red emitting units, so that an overall white emission results. How does white emitting copoly can be synthesized, is described in detail in DE 10343606.
  • Units of the formula (3) are very particularly suitable for the synthesis of phospholuminescent copolymers. These then contain, in addition to the units of the formula (3) according to the invention, units of
  • the proportion of units of group 4 is preferably ⁇ 20%, particularly preferably ⁇ 10% and in particular ⁇ 5%.
  • the polymers according to the invention preferably have from 10 to 10,000, more preferably from 20 to 5000 and in particular from 20 to 2000 repeat units.
  • Non-aromatic C atoms are included in corresponding straight-chain, branched or cyclic alkyl or alkoxy chains, as for example in the description for R 1 with respect to formula (3).
  • Xi, X 2 at each occurrence is a bridge spanning M a cyclic system where Xi is O and X 2 is the group
  • M represents, identically or differently, an aromatic ring system having 2 to 40 C atoms each occurrence, which may be unsubstituted or substituted by one or more R 1 radicals which may be the same or different at each occurrence ,
  • M represents, identically or differently, an aromatic ring system having 2 to 40 C atoms, which may be unsubstituted or substituted by one or more radicals R 1 , which may be identical or different at each occurrence can.
  • Preferred polymers according to the invention comprising units of the formula (3) are characterized in that n, m and p are identical or different 0, 1 or 2 on each occurrence, with the proviso that at least one n or m is equal to 2.
  • Preferred polymers according to the invention are characterized in that they contain units of the formula (3) in which q assumes integer values.
  • Particularly preferred polymers according to the invention are characterized in that they contain units of the formula (3) in which q assumes integer values of ⁇ 10.
  • Particularly preferred polymers according to the invention are characterized in that they contain units of the formula (3) in which q assumes integer values of ⁇ 5.
  • the units of the formula (3) are suitable for various functions in the polymer.
  • they can preferably be used as a polymer backbone or as an emitter.
  • which compounds are particularly suitable for which function is described above all by the substituents X and Y.
  • the substituents R 1 also have an influence on the electronic properties of the units of the formula (3).
  • Examples of preferred units of the formula (3) are the following structures 3.1 to 3.29, in which the linkage in the polymer is indicated in each case by the dashed bonds. These structures can be substituted in all places where substitution is possible. However, possible substituents are not listed for the sake of clarity.
  • the polymers of the invention are homopolymers or copolymers.
  • copolymers according to the invention can potentially have one or more further structures, preferably from the abovementioned groups 1 to 7.
  • copolymers according to the invention may have random, alternating or block-like structures or alternatively have several of these structures in turn. How copolymers with block-like structures can be obtained is described in detail, for example, in WO 05/014688. Coplymeres may also be highly branched or dendrimeric systems.
  • the polymers according to the invention are prepared by polymerization of one or more types of monomer, of which at least one monomer in the polymer leads to units of the formula (3). Corresponding polymerization reactions are in principle many. However, some types have proved particularly useful here, leading to CC or CN linkages:
  • Monomers which lead to polymers according to the invention comprising structural units of the formula (3) and have at the 2,7-position (or in a suitable position on Y, if present) suitable functionalities which allow this monomer unit to be incorporated into the polymer, are new and therefore also the subject of the present invention.
  • the present invention furthermore relates to bifunctional monomeric compounds of the formula (4)
  • the C-C linkages are preferably selected from the groups of the SUZUKI coupling, the YAMAMOTO coupling, the SONOGASHIRA coupling, the HECK coupling and the STILLE coupling.
  • the C-N linkage is preferably a HARTWIGBUCHWALD clutch.
  • the polymer of the invention not as a pure substance, but. to use as a mixture (blend) together with at least one further optional polymeric, oligomeric, dendritic and / or low molecular weight substance.
  • these may, for example, improve the electronic properties, affect the singlet to triplet state transfer, or even emit light from the singlet or triplet state.
  • electronically inert substances may be useful to influence, for example, the morphology of the polymer film formed or the viscosity of polymer solutions. Such blends are therefore also the subject of the present invention.
  • the invention further provides solutions and formulations of at least one inventive polymer or a blends according to the invention in at least one solvent.
  • polymer solutions can be prepared is described, for example, in WO 02/072714, in WO 03/019694 and in the literature cited therein.
  • These solutions can be used to prepare thin polymer layers, for example by surface coating methods (eg spin coating) or printing methods (eg ink jet printing).
  • the polymers of the invention can be used in PLEDs. These contain cathode, anode, emission layer and optionally further layers, such as. B. preferably a Lochinjetechnischs slaughter and optionally an intermediate layer between the Lochinjetechnischs- and the emission layer. How PLEDs can be produced is described in detail as a general method in WO 04/037887, which must be adapted accordingly for the individual case.
  • the polymers according to the invention are particularly suitable as electroluminescent materials in the PLEDs or displays produced in this way.
  • electroluminescent materials are materials which can be used as active layer in a PLED.
  • Active layer means that the layer is able to emit light upon application of an electric field (light-emitting layer) and / or that it improves the injection and / or transport of the positive and / or negative charges (charge injection or charge transport layer). It may also be an intermediate layer between a hole injection layer and an emission layer.
  • the invention therefore also relates to the use of a polymer according to the invention in a PLED, in particular as an electroluminescent material.
  • the invention thus likewise relates to a PLED having one or more active layers, wherein at least one of these active layers contains one or more polymers according to the invention.
  • the active layer may be, for example, a light-emitting layer and / or a transport layer and / or a charge injection layer and / or an intermediate layer.
  • the polymers according to the invention have the following surprising advantages over the poly-spirobifluorenes and polyfluorenes described in WO 03/020790 and in WO 02/077060, which are hereby named as the closest prior art:
  • the polymers according to the invention have higher operative lifetimes, in particular in the case of green and blue-emitting PLEDs.
  • the polymers according to the invention are good electron conductors, even without the use of electron-conducting comonomers. Electron conductive properties in polymers have hitherto been difficult to realize because many prior art electron conductors are not sufficiently stable for high value applications. (5) Since the new polymer backbone of formula (3) itself results in deep blue emission, it is easily possible to introduce emissive units that still produce blue emission in the polymer. This makes it easy to separate charge transport and emission properties in the polymer. This is necessary to stable
  • Example 1 The quantum-mechanical simulations for Example 1, the corresponding ice-linked structure (Example 2) and the derivatives in which q (according to formula (3)) assumes higher values were carried out in order to be able to make statements about the molecular geometry and the position of the energy levels ,
  • Examples 5 and 6 were modeled using the CaChe simulation program (version 6.1). The most energetically stable conformations were found by optimization using AM1 methods. The calculation of the HOMO and LUMO energy levels was also based on the optimized geometries with AM1 methods. All five trimers show very low LUMO energy levels, typically around -3.4 eV. As already explained above, this result raises the strict restriction in the choice of suitable cathode materials.

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  • Chemical & Material Sciences (AREA)
  • Engineering & Computer Science (AREA)
  • Organic Chemistry (AREA)
  • Materials Engineering (AREA)
  • Physics & Mathematics (AREA)
  • Optics & Photonics (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Medicinal Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Microelectronics & Electronic Packaging (AREA)
  • General Physics & Mathematics (AREA)
  • Electroluminescent Light Sources (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)
EP07702866A 2006-01-26 2007-01-18 Materiaux electroluminescents et leur utilisation Ceased EP1977432A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
DE102006003710A DE102006003710A1 (de) 2006-01-26 2006-01-26 Elektrolumineszierende Materialien und deren Verwendung
PCT/EP2007/000429 WO2007085377A2 (fr) 2006-01-26 2007-01-18 Materiaux electroluminescents et leur utilisation

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EP1977432A1 true EP1977432A1 (fr) 2008-10-08

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US (1) US20090032776A1 (fr)
EP (1) EP1977432A1 (fr)
JP (1) JP2009524710A (fr)
KR (1) KR20080091266A (fr)
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KR20080091266A (ko) 2008-10-09
DE102006003710A1 (de) 2007-08-02
JP2009524710A (ja) 2009-07-02

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