EP2817350A2 - Polymères contenant des unités structurales sous forme de dibenzocycloheptane - Google Patents

Polymères contenant des unités structurales sous forme de dibenzocycloheptane

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Publication number
EP2817350A2
EP2817350A2 EP13701370.2A EP13701370A EP2817350A2 EP 2817350 A2 EP2817350 A2 EP 2817350A2 EP 13701370 A EP13701370 A EP 13701370A EP 2817350 A2 EP2817350 A2 EP 2817350A2
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Prior art keywords
polymer
organic
formula
structural units
polymers
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EP13701370.2A
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German (de)
English (en)
Inventor
Anna Hayer
Niels Schulte
Eva Maria Reis
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Merck Patent GmbH
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Merck Patent GmbH
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Priority to EP13701370.2A priority Critical patent/EP2817350A2/fr
Publication of EP2817350A2 publication Critical patent/EP2817350A2/fr
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Definitions

  • the present application relates to polymers containing dibenzocycloheptane structural units, to processes for their preparation and to blends and formulations comprising these polymers.
  • OLEDs organic electroluminescent devices
  • polymeric materials suitable for use in organic electroluminescent devices are known in the art.
  • compounds based on monomer units such as spirobifluorene, fluorene, indenofluorene,
  • organic electroluminescent devices should be further increased, especially in blue emitting systems and for high quality applications.
  • Dibenzocycloheptanechen can be successfully used as materials in electronic devices, preferably organic electroluminescent devices.
  • R 3 in each occurrence, identically or differently H, F, a straight-chain, branched or cyclic Alkyh alkoxy or Thioalkoxy distr having 1 to 40 carbon atoms, in which also one or more H atoms may be replaced by F and in the one or more non-adjacent CH 2 groups may be replaced by O, CO, COO or O (CO) O, or a mono- or polycyclic, aromatic or heteroaromatic ring system; m, n independently of one another, identical or different, can be 0, 1, 2 or 3, preferably 0 or 1 and particularly preferably 0; and the dashed lines are the bonds to the neighboring ones
  • the polymers according to the invention preferably contain from 2 to 10 000 repeat units, the term "polymer” being intended to encompass both polymers and dendrimers and oligomers in the present application
  • the oligomeric compounds according to the invention have from 2 to 9 repeat units
  • Preferred polymers and dendrimers according to the invention contain in total 10 to 10,000 repeat units
  • the degree of branching DB of the polymers and dendrimers may be between 0 (linear polymer without branching points) and 1 (fully branched dendrimer).
  • the polymers according to the invention preferably have a molecular weight M w in the range from 1000 to 2,000,000 g / mol, particularly preferably a molecular weight M w in the range from 100,000 to 1,500,000 g / mol and very particularly preferably a molecular weight M w in the range from 150,000 to 1,000,000 g / mol.
  • GPC gel permeation chromatography
  • the term "mono- or polycyclic, aromatic ring system” in the present application means an aromatic ring system having 6 to 60, preferably 6 to 30, more preferably 6 to 14 and most preferably 6 to 10 aromatic ring atoms, which is not necessarily only contains aromatic groups but in which also several aromatic units by a short non-aromatic unit ( ⁇ 10% of the atoms other than H, preferably ⁇ 5% of the atoms other than H), such as sp 3 -hybridized carbon atom or O or N atom, CO group, etc. may be interrupted, for example, systems such as 9,9 'spirobifluorene, 9,9' -. diarylfluorene, etc. may be understood as aromatic ring systems.
  • the aromatic ring systems may be mono- or polycyclic, i. they may have a ring (e.g., phenyl) or multiple rings which may also be condensed (e.g., naphthyl) or covalently linked (e.g., biphenyl), or a combination of fused and linked rings.
  • a ring e.g., phenyl
  • multiple rings which may also be condensed (e.g., naphthyl) or covalently linked (e.g., biphenyl), or a combination of fused and linked rings.
  • Preferred aromatic ring systems are e.g. Phenyl, biphenyl,
  • Ring system with 5 to 60, preferably 5 to 30, more preferably 5 to 20 and most preferably 5 to 9 understood aromatic ring atoms, wherein one or more of these atoms is / are a heteroatom.
  • the "mono- or polycyclic heteroaromatic ring system” does not necessarily contain only aromatic groups but may also be replaced by a short non-aromatic moiety ( ⁇ 10% of that of H
  • different atoms preferably ⁇ 5% of the atoms other than H
  • heteroaromatic ring systems may be mono- or polycyclic, i. they may have one or more rings, which may also be fused or covalently linked (e.g., pyridylphenyl), or a combination of fused and linked rings. Preference is given to fully conjugated heteroaryl groups.
  • Preferred heteroaromatic ring systems are e.g. 5-membered rings such as pyrrole, pyrazole, imidazole, 1, 2,3-triazole, 1, 2,4-triazole, tetrazole, furan, thiophene, selenophene, oxazole, isoxazole, 1,2-thiazole, 1,3-thiazole , 1, 2,3-oxadiazole, 1, 2,4-oxadiazole, 1, 2,5-oxadiazole, 1, 3,4-oxadiazole, 1, 2,3-thiadiazole, 1, 2,4-thiadiazole, 1 , 2,5-thiadiazole, 1, 3,4-thiadiazole, 6-membered rings such as pyridine, pyridazine, pyrimidine, pyrazine, 1, 3,5-triazine, 1,2,4-triazine, 1, 2,3- Triazine, 1,2,4,5-tetrazine, 1, 2,3,4-tet
  • Benzimidazole benzotriazole, purine, naphthimidazole, phenanthrimidazole, pyridimidazole, pyrazine imidazole, quinoxaline imidazole, benzoxazole,
  • the mono- or polycyclic, aromatic or heteroaromatic ring system may be unsubstituted or substituted. Substituted means in the present application that the mono- or polycyclic, aromatic or heteroaromatic ring system has one or more substituents R 1 .
  • the dashed lines in the formulas (Ia), (Ib) and (Ic) represent the bonds to the adjacent structural units in the polymer.
  • R 1 , R 2 m and n in the formulas (Ia) to (Ic) can in this case for R 1 , R 2 , m and n meanings given in relation to formula (I).
  • a preferred structural unit of the formula (Ia) is characterized by
  • a particularly preferred structural unit of the formula (Ia) is represented by the formula (Ia2) given below.
  • the dashed lines in the formulas (Ia1) and (Ia2) represent the bonds to the adjacent structural units in the polymer.
  • the radicals R 1 in the formulas (Ia1) and (Ia2) can in this case correspond to those for R 1 in relation to formula ( I) assume accepted meanings.
  • R 1 and R 2 in the formulas (I), (Ia) to (Ic) and (Ia1) and (Ia2) at each occurrence identically or differently, a straight-chain or branched alkyl or alkoxy group having 1 to 10 C Atoms, more preferably having 1 to 6 carbon atoms.
  • the polymer according to the invention in addition to one or more structural units of the formula (I), also contains at least one further structural unit which is different from the structural unit of the formula (I).
  • these are under Others such as those in WO 02/077060 A1 and in WO
  • Group units containing the hole injection and / or
  • Group 3 Units that are combinations of individual units of the group
  • Group 4 units which the emission characteristics so far
  • Electrofluorescence can be obtained
  • Group 5 units that improve the transition from the singlet triplet state
  • Group 6 Units indicating the emission color of the resulting
  • Group 7 units typically used as polymer backbone
  • Group 8 units containing the film morphology and / or the
  • Have hole transport properties are, for example, triarylamine, benzidine, tetraaryl-para-phenylenediamine, triarylphosphine,
  • these arylamines and heterocycles lead to a HOMO in the polymer of greater than -5.8 eV (at vacuum level), more preferably greater than -5.5 eV.
  • Group 2 structural units which have electron injection and / or electron transport properties are, for example, pyridine, pyrimidine, pyridazine, pyrazine, oxadiazole, quinoline, quinoxaline,
  • these units in the polymer result in a LUMO of less than -1.5 eV (vs. vacuum level), more preferably less than -2.0 eV.
  • the polymers according to the invention may contain units from group 3 in which structures which influence the hole mobility and which electron mobility are involved (ie units from groups 1 and 2) are bonded directly to one another or structures are contained affect both hole mobility and electron mobility. 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 so-called triplet emitter units, are those which can emit light at room temperature with high efficiency from the triplet state, ie
  • a triplet emitter unit is understood in the present application to mean a compound which comprises a triplet emitter.
  • triplet emitters are understood as meaning all compounds which are capable of undergoing transition from one triplet state to one energetically lower state to emit light in the visible or NIR range. This is also called phosphorescence.
  • Compounds which contain heavy atoms with an atomic number of more than 36 are suitable for this purpose.
  • Preference is given to compounds which contain d- or f-transition metals which fulfill the abovementioned condition.
  • Particular preference is given here to corresponding structural units which contain elements of group 8 to 10 of the periodic table (Ru, Os, Rh, Ir, Pd, Pt).
  • Structural units for the polymers according to the invention can be found here e.g. various complexes, such as e.g. in WO 02/068435 A1, in WO 02/081488 A1 and in EP 1239526 A2. Corresponding monomers are described in WO 02/068435 A1 and in WO 2005/042548 A1. According to the invention, it is preferred to use triplet emitters which emit in the visible spectral range (red, green or blue). The triplet emitter may be part of the backbone of the polymer (i.e., in the backbone of the polymer) or it may be located in a side chain of the polymer.
  • Group 5 structural units are those which improve the transition from the singlet to the triplet state and which, in support of the abovementioned triplet emitter units, use the
  • Carbazole and bridged carbazole dimer units are particularly suitable for this purpose, as are described, for example, in US Pat. in WO 2004/070772 A2 and in WO 2004/113468 A1. Furthermore come for this ketones, phosphine oxides, sulfoxides, sulfones, silane derivatives and the like
  • Group 6 structural units are, in addition to the above, those having at least one more aromatic or other conjugated structure other than those mentioned above. Groups fall, i. which only slightly affect the charge carrier mobilities, which are not organometallic complexes or which do not affect the
  • Particularly preferred is the incorporation of 1, 4 phenylene, 1, 4-naphthylene, 1, 4 or 9,10-anthrylene, 1, 6, 2,7- or 4,9-pyrenylene, 4th , 4'-biphenylylene, 4,4 "-terphenyl, 4,4'-bi-1, 1'-naphthylylene, 4,4'-tolanylene, 4,4'-stilbenylene, 4,4" Bisstyryl-arylene, benzothiadiazole and corresponding oxygen derivatives, quinoxaline, phenothiazine, phenoxazine, dihydrophenazine,
  • Pentacene or perylene derivatives which are preferably substituted, or preferably conjugated push-pull systems (systems substituted with donor and acceptor substituents) or systems such as squarins or quinacridones, which are preferably substituted.
  • Group 7 structural units are units having aromatic structures of 6 to 40 carbon atoms, which are typically used as a backbone
  • 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 cis- and trans- indenofluorene derivatives, but
  • Group 8 structural units are those which influence the film morphology and / or the rheology of the polymers, e.g. Siloxanes, long alkyl chains or fluorinated groups, but also particularly rigid or flexible units, such as e.g. liquid crystal forming units or
  • Preferred polymers according to the invention are those in which
  • At least one structural unit has charge transport properties, ie polymers which contain, inter alia, at least one unit selected from groups 1 and 2.
  • Preferred compounds according to the invention are polymers which, in addition to structural units of the formula (I), additionally contain one or more units selected from groups 1 to 8. It may also be preferred that at the same time more than one structural unit is present in a group.
  • Improve charge injection ie units from group 1 and / or 2; particularly preferred is a proportion of 0.5 to 50 mol% of these units; very particular preference is given to a proportion of from 1 to 30 mol% of these
  • the polymers according to the invention contain structural units from group 7 and units from group 1 and / or 2. It is particularly preferred if the sum of structural units of the formula (I), of units of group 7 and units of group 1 and / or 2 of the polymer is at least 50 mol%, based on all units of the polymer
  • a polymerization reaction is generally carried out with one or more different monomer units, wherein at least one monomer incorporated in the polymer leads to structural units of the formula (I).
  • NEGISHI, SONOGASHIRA, HIYAMA, ULLMANN, WITTIG, or HARTWIG BUCHWALD polymerisation is known to the person skilled in the art and described in the literature, for example in WO 03/048225 A2, in WO 2004/037887 A2 and in US Pat WO 2004/037887 A2 described in detail.
  • dendrimers according to the invention are characterized by being prepared by SUZUKI, YAMAMOTO, STILLE, HECK, NEGISHI, SONOGASHIRA, HIYAMA, ULLMANN, WITTIG, or HARTWIG-BUCHWALD polymerization.
  • the dendrimers according to the invention can be prepared according to methods known to the person skilled in the art or in analogy thereto.
  • Monomers which lead to structural units of the formula (I) in the polymers according to the invention are compounds which are correspondingly substituted and have at two positions suitable functionalities which make it possible to incorporate this monomer unit in the polymer.
  • X represents a chemical functionality which is identically or differently selected from the class of the halogens, O-tosylates, O-triflates, O-sulfonates, boric acid esters, partially fluorinated silyl groups,
  • the backbone of the monomer compounds can be functionalized by standard methods, for example by Friedel-Crafts alkylation or acylation.
  • the skeleton can be halogenated according to standard methods of organic chemistry.
  • the halo- genated compounds can optionally be further implemented in additional functionalization steps. For example, the
  • halogenated compounds are used either directly or after conversion into a boronic acid derivative or organotin derivative as starting materials for the reaction to polymers, oligomers or dendrimers.
  • the methods mentioned are merely a selection of the reactions known to the person skilled in the art which, without being inventive, can be used for the synthesis of the compounds according to the invention.
  • polymers according to the invention may be preferred not to use as a pure substance but as a mixture (blend) together with further any desired polymeric, oligomeric, dendritic or low molecular weight substances. These may e.g. the electronic
  • a mixture is understood above and below to mean a composition which contains at least one polymeric component.
  • Another object of the present application is thus a mixture (blend) containing one or more polymers of the invention, and one or more other polymeric, oligomeric, dendritic or low molecular weight substances.
  • a mixture contains a polymer according to the invention comprising structural units of the formula (I) and a low molecular weight substance.
  • a mixture contains a polymer according to the invention, an emitter which is either present in the polymer according to the invention or, as in the abovementioned embodiments, mixed in as low molecular weight substance, and further low molecular weight substances.
  • These low molecular weight substances can have the same functionalities as have been mentioned for possible monomer units in groups 1 to 8.
  • the present application furthermore relates to formulations comprising one or more polymers according to the invention and at least one solvent. How to make such solutions can, is known in the art and for example in the WO
  • Suitable and preferred solvents are, for example, toluene, anisoles, xylenes, ethylbenzoate, dimethylanisoles, mesitylenes, tetralin, veratrole and tetrahydrofuran or mixtures of these
  • These solutions can be used to prepare thin polymer layers, for example by area-coating techniques (e.g., spin-coating) or by printing techniques (e.g., ink-jet printing).
  • area-coating techniques e.g., spin-coating
  • printing techniques e.g., ink-jet printing
  • the polymers, mixtures and formulations according to the invention can be used in electronic or optoelectronic devices or for their production.
  • the present application relates to the use of the polymers, mixtures and formulations according to the invention in electronic or optoelectronic devices, preferably in organic electroluminescent devices (OLED), organic light-emitting electrochemical cells (OLEC), organic field-effect transistors (OFETs), organic integrated circuits ( O-ICs), organic thin-film transistors (TFTs), organic solar cells (O-SCs), organic laser diodes (O-lasers), organic photovoltaic elements or devices (OPV) or organic photoreceptors (OPCs), particularly preferably in organic electroluminescent devices ( OLED).
  • OLED organic electroluminescent devices
  • OEC organic light-emitting electrochemical cells
  • OFFETs organic field-effect transistors
  • O-ICs organic integrated circuits
  • TFTs organic thin-film transistors
  • O-SCs organic solar cells
  • O-lasers organic laser diodes
  • O-lasers organic photovoltaic elements or devices
  • OPCs organic photoreceptors
  • the present application is focused on the use of the compounds according to the invention in organic electroluminescent devices (OLEDs).
  • OLEDs organic electroluminescent devices
  • the polymer, oligomer or dendrimer according to the invention is present as a layer (or in a layer) in the electronic device.
  • the present application thus also relates to a layer, in particular an organic layer, comprising one or more polymers according to the invention.
  • the compounds are used in organic electronic devices containing at least one layer containing one or more of the polymers of the invention.
  • the use is particularly preferred in organic electroluminescent devices containing anode, cathode and at least one
  • At least one layer contains at least one inventive polymer having structural units of the formula (I).
  • the mixture of the polymer containing structural units of the formula (I) and the emitting compound then contains between 99 and 1% by weight, preferably between 98 and 60% by weight, particularly preferably between 97 and 70% by weight, very particularly preferably between 95 and 75 wt .-% of the polymer based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99 wt .-%, preferably between 2 and 40 wt .-%, particularly preferably between 3 and 30 wt .-%, most preferably between 5 and 25 wt .-% of the emitter based on the Total mixture of emitter and matrix material.
  • the polymers according to the invention are used as hole transport material or as hole injection material.
  • the polymer is preferably used in a hole transport or in a hole injection layer.
  • these hole injection layers according to the invention are triarylamines, carbazoles, silanes or phosphanes.
  • a hole injection layer in the sense of the present application is a layer which directly adjoins the anode.
  • a hole transport layer in the sense of the present application is a layer that lies between a hole injection layer and an emission layer.
  • Polymers according to the invention can be used as hole transport or as hole injection material, it may be preferred if they are with
  • Electron-acceptor compounds are doped, for example with F 4 -Tetracyanochinodimethan (TCNQ) or with compounds as described in EP 1476881 or in EP 1596445.
  • TCNQ F 4 -Tetracyanochinodimethan
  • polymers of the invention can be used in charge blocking layers.
  • charge blocking layers may consist of various suitable materials,
  • This layer which is generally applied by known coating techniques, may be of any effective thickness, preferably in the range of 0.05 to 0.5 ⁇ m.
  • the present application furthermore relates to electronic or optoelectronic components, preferably organic electroluminescent devices (OLED), organic light-emitting electrochemical cells (OLEC), organic field-effect transistors (OFETs), organic integrated circuits (O-ICs), organic thin film transistors (TFTs), organic solar cells (O-SCs), organic laser diodes (O-lasers), organic photovoltaic elements or devices (OPV) or organic photoreceptors (OPCs), more preferably organic electroluminescent devices with one or more active ones
  • OLED organic electroluminescent devices
  • OEC organic light-emitting electrochemical cells
  • OFFETs organic field-effect transistors
  • O-ICs organic integrated circuits
  • TFTs organic thin film transistors
  • O-SCs organic solar cells
  • O-lasers organic laser diodes
  • O-lasers organic photovoltaic elements or devices
  • OPCs organic photoreceptors
  • the active layer may, for example, be a light-emitting layer, a charge-transport layer and / or a charge-injection layer.
  • OLEDs can be produced is known to the person skilled in the art and is described in detail, for example, as a general method in WO 2004/070772 A2, which is to be adapted accordingly for the individual case.
  • an organic electroluminescent device characterized in that one or more layers of solution, such as by spin coating, or with any printing method, such as roll to roll, screen printing, flexographic printing or offset printing, but particularly preferably LITI (Light Induced Thermal Imaging, Thermal transfer printing), ink-jet printing (ink-jet printing), dipping method or spraying method.
  • LITI Light Induced Thermal Imaging, Thermal transfer printing
  • ink-jet printing ink-jet printing
  • spraying method soluble compounds are needed.
  • substitutions according to the invention make it possible to achieve a high solubility.
  • the organic electroluminescent device may contain further layers. These may be selected, for example, from charge carrier injection, charge carrier transport or carrier blocking layer (T. Matsumoto et al., Multiphoton Organic EL Device Having Charge Generation Layer, IDMC 2003, Taiwan, Session 21 OLED (5)). But be it
  • the organic electroluminescent device comprises a plurality of emitting layers, wherein at least one layer contains at least one inventive polymer.
  • the emission layers preferably have a plurality of emission maxima between 380 nm and 750 nm, so that overall white emission results in this case.
  • three-layer systems wherein at least one of these layers contains at least one polymer according to the invention and wherein the three layers show blue, green and orange or red emission (for the basic structure see eg WO 05/011013).
  • the subject of the present application are thus both the
  • the compounds according to the invention preferably have one or more of the following advantageous properties:
  • the polymers of the invention have a large band gap
  • the compounds according to the invention increase the lifetime and the efficiency of, in particular, blue-emitting organic compounds
  • Electroluminescent devices for high-quality applications are Electroluminescent devices for high-quality applications.
  • the monomeric compounds for the synthesis of the polymers according to the invention can be prepared by methods described in the prior art, it being possible for the person skilled in the art to apply the methods to the actual case without being inventive.
  • the dibenzocycloheptane monomer used in the polymer of the invention is obtained by the following route:
  • PLED polymeric organic light-emitting diode
  • ITO structure indium-tin-oxide, a transparent, conductive anode
  • sodalimeglass that result in four pixels a 2 x 2 mm with the vapor deposited at the end of the manufacturing process.
  • PEDOT is a polythiophene derivative (Baytron P VAI 4083sp.) From H. C. Starck, Goslar, which is supplied as an aqueous dispersion) is likewise applied by spin coating in the clean room.
  • the required spin rate depends on the degree of dilution and the specific spincoater geometry (typically 80 nm: 4500 rpm).
  • the substrates are baked for 10 minutes at 180 ° C on a hot plate. Thereafter, under an inert gas atmosphere (nitrogen or argon), initially 20 nm of an interlayer (typically a
  • Deposition mask vapor deposited high purity metals from Aldrich, particularly barium 99.99% (order no 474711). Coaters of Lesker above, typical vacuum level 5 x 10 "6 mbar). In order to protect especially the cathode against air and humidity, is Finally, the devices are encapsulated and then characterized by mounting the devices in holders specially designed for the substrate size and contacting them with spring contacts
  • Photodiode with eye-tracking filter can be placed directly on the measuring holder to exclude the influence of extraneous light.
  • the voltages are from 0 to max. 20 V in 0.2 V increments and lowered again. For each measuring point, the current through the device as well as the received photocurrent of the
  • Photodiode measured In this way one obtains the IVL data of the test devices. Important parameters are the measured efficiency at 000 cd / m 2 (in cd / A) and the voltage required for 1000 cd / m 2 .
  • the polymer according to the invention has both a higher efficiency and a significantly longer service life than a comparable polymer of the prior art.
  • the polymer according to the invention leads to a deeper blue emission.

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  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Electroluminescent Light Sources (AREA)
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  • Other Resins Obtained By Reactions Not Involving Carbon-To-Carbon Unsaturated Bonds (AREA)

Abstract

Polymères contenant des unités structurales sous forme de dibenzocycloheptane, procédé de production desdits polymères, et mélanges et formulations les contenant. La présente invention concerne en outre l'utilisation des polymères ou mélanges décrits dans des dispositifs électroniques, ainsi que des dispositifs électroniques, en particulier des diodes électroluminescentes organiques, contenant les polymères ou mélanges décrits.
EP13701370.2A 2012-02-22 2013-01-26 Polymères contenant des unités structurales sous forme de dibenzocycloheptane Withdrawn EP2817350A2 (fr)

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EP12001158 2012-02-22
PCT/EP2013/000232 WO2013124029A2 (fr) 2012-02-22 2013-01-26 Polymères contenant des unités structurales sous forme de dibenzocycloheptane
EP13701370.2A EP2817350A2 (fr) 2012-02-22 2013-01-26 Polymères contenant des unités structurales sous forme de dibenzocycloheptane

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US20150014598A1 (en) 2015-01-15
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WO2013124029A2 (fr) 2013-08-29

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