WO2010054728A1 - Materialien für organische elektrolumineszenzvorrichtungen - Google Patents
Materialien für organische elektrolumineszenzvorrichtungen Download PDFInfo
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- 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
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- 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
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- H10K2101/00—Properties of the organic materials covered by group H10K85/00
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- Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
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- Y02E10/50—Photovoltaic [PV] energy
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- Y10S—TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
- Y10S428/00—Stock material or miscellaneous articles
- Y10S428/917—Electroluminescent
Definitions
- the present invention relates to transition metal complexes of the general formulas I or II, in particular as emitter molecules in organic electronic devices, to a layer and to an electronic device which contain the compounds according to the invention, and to a process for preparing the compounds according to the invention.
- Chelate complexes and organometallic compounds are used as functional materials in a number of different applications, which can be attributed to the electronics industry in the broadest sense.
- organic electroluminescent devices based on organic components (general description of the structure, cf., US Pat. Nos. 4,539,507 and 5,151,629) or their individual components, the organic light-emitting diodes (OLEDs), the market introduction has already taken place. Despite the successes already achieved, further improvements are desirable here.
- organometallic complexes which exhibit phosphorescence rather than fluorescence are increasingly being discussed (M.A. Baldo, S. Lamansky, P.E. Burrows, M.E. Thompson, S.R. Forrest, Appl. Phys. Lett., 1999, 75, 4-6).
- organometallic compounds As essential conditions for the practical application here are in particular a high operating life, a high stability against temperature load and a low application and operating voltage to enable mobile applications to call.
- the class of known metal complexes has general weak points, which are briefly outlined below: Many of the known metal complexes have low thermal stability (see: RG Charles, J. Inorg., Nucl. Chem., 1963, 25, 45). In the case of vacuum deposition, this inevitably always leads to the release of organic pyrolysis products, which in some cases considerably reduce the operational lifetime of OLEDs even in small quantities.
- Metal complexes of the transition metals of group 10 in which the central metal has two aromatic N and two C atoms (WO 2004/108857, WO 2005/042550 , WO 2005/042444, US 2006/0134461 A1) or two imine-like N atoms in combination with two phenolic O atoms (WO 2004/108857) or via two aromatic N and two basic N atoms (WO 2004/108857) is bound.
- the known compounds have, inter alia, electroluminescence in the blue, red and green regions of the electromagnetic spectrum.
- the object of the invention was thus to provide such compounds.
- the present invention provides a compound of general formula I.
- M is a metal ion of oxidation state +2
- Ar is the same or different at each occurrence an aromatic or heteroaromatic ring system which may be substituted by one or more arbitrary radicals R and the ring systems Ar may optionally be linked together by single bonds or any radicals R, - A -
- Y is the same or different at each occurrence C, N or P, with the proviso that always two C atoms and two N atoms or always two C atoms and two P atoms are bound to the metal,
- R may be substituted R, or combinations thereof,
- R 1 the same or different at each occurrence, is an arbitrary radical
- the present invention further provides a compound of general formula II
- M is a metal ion of oxidation state +2
- Ar is the same or different at each occurrence an aromatic or heteroaromatic ring system which may be substituted by one or more arbitrary radicals R and the ring systems Ar may optionally be linked together by single bonds or any radicals R,
- Y is the same or different at each occurrence C, N or P, with the proviso that always two C atoms and two N atoms or always two C atoms and two P atoms are bound to the metal,
- R may be substituted R, or combinations thereof,
- R 1 the same or different at each occurrence, is an arbitrary radical
- Ar is the same or different at each occurrence, an aromatic or heteroaromatic ring system which may be substituted with one or more of any R radicals, and the ring systems Ar are optionally substituted by single bonds or any of them
- Radicals R can be linked to one another
- X is the same or different at each occurrence, a bivalent group selected from
- R which may be substituted by one or more radicals R, or combinations thereof;
- Ar 1 identical or different at each occurrence, an aromatic or heteroaromatic ring system having 5 to 40 aromatic ring atoms, which may be substituted by one or more non-aromatic radicals R,
- R 1 is the same or different at each occurrence H, D, F, CF 3 , CN, an alkyl, alkoxy or thioalkoxy group having 1 to 40 carbon atoms or a branched or cyclic alkyl, alkoxy or thioalkoxy group having 3 to 40 C atoms, each of which may be substituted with one or more R 2 radicals, one or more non-adjacent
- R 2 is identical or different at each occurrence H, D, F, CN or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H atoms may be replaced by F, where two or more substituents R 2 also together form a mono- or polycyclic aliphatic or aromatic ring system.
- M is Pd or Pt. More preferably, M is Pt.
- Ar is identical or different at each occurrence, an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may be substituted by a plurality of radicals R,
- X is the same or different at each occurrence, a bivalent group selected from
- aromatic or heteroaromatic ring system having from 5 to 15 aromatic ring atoms selected from
- R is identical or different at each occurrence N (Ar 1 ) 2 , CN, a straight-chain alkyl group having 1 to 3 C atoms, or an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, each by one or more radicals R 2 can be substituted,
- R 1 is identical or different at each occurrence H, D, CN, an alkyl group having 1 to 10 C atoms, or an aromatic or heteroaromatic ring system having 5 to 10 aromatic ring atoms, which may be substituted by one or more radicals R 2 ,
- R 2 is identical or different at each occurrence H 1 F, CN or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 10 C-atoms, wherein two or more substituents R 2 together also a mono- or polycyclic aliphatic or aromatic ring system can form, and
- Ar 1 is as defined above.
- radicals and indices defined above occur several times within a compound, the radicals independently of one another on each occurrence may be the same or different, as defined.
- An aryl group in the sense of this invention contains 6 to 60 C atoms;
- a heteroaryl group contains 2 to 60 C atoms and at least one heteroatom, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
- the heteroatoms are preferably selected from N, O and / or S.
- a simple aromatic cycle ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused (fused) aryl or heteroaryl group, for example naphthalene,
- Particularly preferred for the purposes of this invention is the group Ar in the general formulas I or II benzene, naphthalene, pyridine, pyrimidine, pyrazine, pyridazine, quinoline, isoquinoline, furan, thiophene, pyrrole,
- Benzofuran, benzothiophene and indole most preferably benzene, naphthalene, pyridine, quinoline and isoquinoline.
- naphthalene, quinoline, benzothiophene, benzofuran and indole are preferred, naphthalene and quinoline are particularly preferred.
- An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
- a heteroaromatic ring system in the sense of this invention contains 2 to 60 C atoms and at least one heteroatom in the ring system, with the proviso that the sum of C atoms and heteroatoms gives at least 5.
- the heteroatoms are preferably selected from N, O and / or S.
- An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups Heteroaryl groups by a non-aromatic unit (preferably less than 10% of the atoms other than H), such as.
- As an sp 3 -hybridized C, N or O atom may be interrupted.
- systems such as 9,9'-spirobifluorene, 9,9-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc. are to be understood as aromatic ring systems in the context of this invention, and also systems in which two or more aryl groups, for example by a linear or cyclic alkyl group or interrupted by a silyl group.
- An aromatic or heteroaromatic ring system having 5-60 aromatic ring atoms, which may be substituted in each case by the abovementioned radicals R 1 and which may be linked via any position on the aromatic or heteroaromatic compounds, is understood in particular to mean groups derived from benzene , Naphthalene, anthracene, benzanthracene, phenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenyls, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydropyrene, cis- or trans-indenofluorene, truxene, Isotruxene, spirotruxene, spiroisotruxene, furan, benzofur
- an aliphatic hydrocarbon radical or an alkyl group which may typically contain from 1 to 40 or even from 1 to 20 carbon atoms, and in which individual H atoms or CH 2 groups are also substituted by the abovementioned groups prefers the radicals methyl, ethyl, n-propyl, i-propyl, n-butyl, i-butyl, s-butyl, t-butyl, 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
- alkoxy group having 1 to 40 carbon atoms methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy, n-pentoxy, s-pentoxy, 2-methylbutoxy, n-hexoxy, cyclohexyloxy, n-heptoxy, cycloheptyloxy, n-octyloxy, cyclooctyloxy, 2-ethylhexyloxy, pentafluoroethoxy and 2,2,2-trifluoroethoxy understood.
- one or more H atoms can also be replaced by F, Cl, Br, I, CN or NO 2 , preferably F, Cl or CN, more preferably F or Cl, particularly preferably F.
- M, X, Y, R and R 1 are as defined above and Z is the same or different at each occurrence is CR or N, more preferably CR.
- the compounds according to the invention are preferably quadratic planar complexes which contain a four-coordinate metal ion in the oxidation state +2.
- the metal is preferably selected from metals of the 10th group of the Periodic Table of the Elements, in particular Pd and R.
- the compounds according to the invention have a triplet emission and have a very good lifetime, high efficiency, high stability to thermal loading and a high Tg (glass transition temperature).
- the invention also provides a process for the preparation of a compound of general formula I or II
- the compounds according to the invention of the formula I or II can be prepared by synthesis steps which are generally known to the person skilled in the art.
- the starting point for ligand synthesis can be, for example, the N-phenylbenzaldimines (Tetrahedron Lett. 2007, 48 (40), 7177-7180), N, N'-dibenzylidene-o-phenylenediamines (J. Chem. Res. 2006, ( 1), 1 -2), N, N'-bis (2-naphthalenylmethylene) -1, 2-benzene-diaminediene (J. Indian Chem. Soc. 2002, 79 (6), 502-504) and N.N'-DKbenzylidene J-i . ⁇ -diaminonaphthalene (Toxicological and Environmental Chemistry 2006, 88 (4), 579-586).
- N-phenylbenzaldimines Tetrahedron Lett. 2007, 48 (40), 7177-7180
- N, N'-dibenzylidene-o-phenylenediamines J. Chem. Res. 2006, ( 1), 1 -2
- a reaction with the corresponding metal (such as Pt or Pd) 1 which is usually used as a solution of a suitable metal salt, for example ⁇ PtCl 4 or KaPdCl 4 .
- the invention also relates to the use of the compounds according to the invention in an organic electronic device, in particular as an emitting compound.
- the invention also relates to the use of the compounds according to the invention as charge transport material and / or charge injection material, preferably in a corresponding layer.
- charge transport material and / or charge injection material, preferably in a corresponding layer.
- These can be either hole transport layers, hole injection layers, electron transport layers or electron injection layers.
- the use as a charge blocking material is possible.
- the organic electronic device contains anode, cathode and at least one layer which contains at least one organic or organometallic compound. However, the device may also contain inorganic materials.
- the compound of formula I or II is present in the electronic device within a layer.
- the invention thus also provides a layer containing a compound of the formula I or II, as defined above.
- the organic electroluminescent device includes cathode, anode and at least one emitting layer. In addition to these layers, they may also contain further layers, for example one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, exciton blocking layers and / or charge generation layers (Charge Generation Layers, IDMC 2003, Taiwan, Session 21 OLED (5), T. Matsumoto, T. Nakada, J. Endo, K. Mori, N. Kawamura, A. Yokoi,
- interlayer can be introduced between two emitting layers, which have, for example, an exciton-blocking function. It should be noted, however, that not necessarily each of these layers must be present. These layers may contain compounds of general formula I or II as defined above.
- the compound according to formula I or II is used as an emitting compound in an emitting layer or as a charge transport compound in a charge transport layer.
- the organic electroluminescent device may contain an emitting layer, or it may contain a plurality of emitting layers, wherein at least one emitting layer contains at least one compound according to formula I or II, as defined above. If there are multiple emission layers, these preferably have a total of several emission maxima between 380 nm and 750 nm, so that a total of white emission results, ie in the emitting layers different emitting compounds are used, which can fluoresce or phosphoresce. Particularly preferred are three-layer systems, the three
- the device may further include a plurality of charge transport layers.
- the compound according to formula I or II When the compound according to formula I or II is used as the emitting compound in an emitting layer, it is preferably used in combination with one or more compounds acting as a matrix.
- the mixture of the compound according to formula I or II and the matrix material in these cases contains between 1 and 99% by weight, preferably between 2 and 90% by weight, more preferably between 3 and 40% by weight, in particular between 5 and 15 wt .-% of the compound according to formula I or II based on the total mixture of emitter and matrix material.
- the mixture contains between 99 and 1 wt .-%, preferably between 98 and 10 wt .-%, particularly preferably between 97 and 60 wt .-%, in particular between 95 and 85 wt .-% of the matrix material based on the total mixture of Emitter and matrix material.
- Preferred matrix materials are aromatic ketones, aromatic phosphine oxides or aromatic sulfoxides or sulfones, e.g. B. according to WO 04/013080, WO 04/093207, WO 06/005627 or the non-disclosed application DE 102008033943.1, triarylamines, carbazole derivatives, z. CBP (N, N-biscarbazolylbiphenyl) or the carbazole derivatives disclosed in WO 05/039246, US 2005/0069729, JP 2004/288381, EP 1205527 or WO 08/086851, indolocarbazole derivatives, e.g. B.
- a compound according to formula I or II as emitter material in combination with two or more different matrix materials are the abovementioned preferred compounds.
- an organic electroluminescent device wherein one or more layers are coated by a sublimation process.
- the materials are vacuum deposited in vacuum sublimation at a pressure less than 10 "5 mbar, preferably less than 10 " 6 mbar, more preferably less than 10 "7 mbar.
- an organic electroluminescent device characterized in that one or more layers are coated with the OVPD (Organic Vapor Phase Deposition) method or with the aid of a carrier gas sublimation.
- the materials are applied at a pressure between 10 ⁇ 5 mbar and 1 bar.
- OVJP Organic Vapor Jet Printing
- the materials are applied directly through a nozzle and thus structured (for example, BMS Arnold et al., Appl. Phys. Lett., 2008, 92, 053301).
- an organic electroluminescent device characterized in that one or more layers of solution, such. B. by spin coating, or with any printing process, such.
- any printing process such as screen printing, flexographic printing or offset printing, but more preferably LITI (Light Induced Thermal Imaging, thermal transfer printing) or inkjet printing (ink jet printing), are produced.
- LITI Light Induced Thermal Imaging, thermal transfer printing
- inkjet printing ink jet printing
- soluble compounds are necessary, which are obtained for example by suitable substitution.
- the compounds according to the invention described above in particular compounds which are substituted or functionalized with reactive groups, can be used as monomers for producing corresponding oligomers, dendrimers or polymers.
- Another object of the invention are therefore oligomers, polymers or dendrimers containing one or more compounds of formula I or II, as defined above, wherein one or more bonds of the compounds of formula I or II to the polymer, oligomer or dendrimer are present.
- the complex therefore forms a side chain of the oligomer or polymer or is linked in the main chain.
- the polymers, oligomers or dendrimers may be conjugated, partially conjugated or non-conjugated.
- the oligomers or polymers may be linear, branched or dendritic.
- the functionalized compounds of the formulas I or II are homopolymerized or copolymerized with further monomers. Preference is given to copolymers in which the compounds of the formula I or II are preferably present at from 0.01 to 50 mol%, particularly preferably in the range from 0.1 to 20 mol%.
- Suitable and preferred comonomers which form the polymer backbone are selected from fluorenes (for example according to EP 842208 or WO 00/22026), spirobifluorenes (for example according to EP 707020, EP 894107 or WO 06/061181), para- phenylenes (for example according to WO 92/18552), carbazoles (for example according to WO 04/070772 or WO 04/113468), thiophenes (for example according to EP 1028136), dihydrophenanthrenes (for example according to WO 05/014689), ice and trans indenofluorenes (for example according to WO 04/041901 or WO 04/113412), ketones (for example according to WO 05/040302), phenanthrenes (for example according to WO 05 / 104264 or WO 07/017066) or even more of these units.
- fluorenes for example according to EP 842208 or
- the proportion of these units in total is preferably in the range of at least 50 mol%.
- the polymers, oligomers and dendrimers may also contain other units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.
- Such polymers containing compounds of general formula I or II can be used for the production of PLEDs, in particular as emitter layer in PLEDs.
- the production of a polymeric emitter layer can be effected, for example, by coating from solution (spin coating or printing process).
- the compounds of this invention have high thermal stability.
- Organic electroluminescent devices containing compounds according to formula I or II as emitting materials have an excellent lifetime.
- Blue, red and green phosphorescent complexes are available which have a deep blue, efficient red or even green emission color and have a long lifetime when used in organic electroluminescent devices. This is a significant advance over the prior art, since until now blue, red and green phosphorescent devices have only poorly colored coordinates and, in particular, a very poor lifetime.
- the compounds according to the invention used in organic electroluminescent devices, lead to high efficiencies and steep current-voltage curves with simultaneously low threshold voltage.
- a solution of appropriate imine ligand (4.1 mmol) in 130 ml of acetic acid is added under N 2 to a solution of 1.7 g of KaPtCl 4 (4.1 mmol) in 130 ml of acetic acid and stirred at 90 ° C. for 3 days. After filtration, the solid is dried in vacuo and then recrystallized under inert gas.
- Electroluminescent devices according to the invention can be prepared as described, for example, in WO 05/003253. Here the results of different OLEDs are compared.
- the basic structure, the materials used, the degree of doping and their layer thicknesses are identical for better comparability.
- the first device example describes a comparison standard according to the prior art, in which the emission layer consists of the host material spiro-ketone and the guest material (dopant) Ir (ppy) 3 or a compound according to the invention.
- the host material is in each case spiro ketone.
- OLEDs are produced with the following structure:
- HIL Hole Injection Layer 20 nm 2,2 ', 7,7'-tetrakis (di-para-tolylamino) spiro-9,9'-bifluorene
- HTL Hole transport layer 20 nm NPB (N-naphthyl-N-phenyl-4,4 1 -diaminobiphenyl)
- Emission layer 40 nm Host: spiro-ketone (SK) (bis (9,9 '- spirobifluorene-2-yl) ketone) dopant: Ir (ppy) 3 (10% doping, vapor-deposited; synthesized according to WO 03/0068526 ) or compound of the invention.
- SK spiro-ketone
- Ir (ppy) 3 10% doping, vapor-deposited; synthesized according to WO 03/0068526
- OLEDs are characterized by default; For this purpose, the electroluminescence spectra, the efficiency (measured in cd / A) as a function of the brightness, calculated from current-voltage-brightness characteristics (ILJL characteristics), and the lifetime are determined. Table 2 summarizes the results of the device measurement. The devices containing the compounds according to the invention show an improved lifetime with comparable efficiency. Table 2: Device results with spiro-ketone as host material and with lr (ppy) 3 or compounds according to the invention as dopant
Abstract
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EP09737354A EP2344511A1 (de) | 2008-11-13 | 2009-10-14 | Materialien für organische elektrolumineszenzvorrichtungen |
US13/001,863 US9217006B2 (en) | 2008-11-13 | 2009-10-14 | Materials for organic electroluminescent devices |
CN2009801251324A CN102076702A (zh) | 2008-11-13 | 2009-10-14 | 有机电致发光器件用材料 |
JP2011535893A JP2012508699A (ja) | 2008-11-13 | 2009-10-14 | 有機エレクトロルミネッセンスデバイス用材料 |
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EP2344511A1 (de) | 2011-07-20 |
TW201031733A (en) | 2010-09-01 |
DE102008057051A1 (de) | 2010-05-20 |
US9217006B2 (en) | 2015-12-22 |
DE102008057051B4 (de) | 2021-06-17 |
KR20110085876A (ko) | 2011-07-27 |
US20110108822A1 (en) | 2011-05-12 |
CN102076702A (zh) | 2011-05-25 |
JP2012508699A (ja) | 2012-04-12 |
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