WO2010099852A1 - Metallkomplexe mit azaborol-liganden und elektronische vorrichtung damit - Google Patents
Metallkomplexe mit azaborol-liganden und elektronische vorrichtung damit Download PDFInfo
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- WO2010099852A1 WO2010099852A1 PCT/EP2010/000635 EP2010000635W WO2010099852A1 WO 2010099852 A1 WO2010099852 A1 WO 2010099852A1 EP 2010000635 W EP2010000635 W EP 2010000635W WO 2010099852 A1 WO2010099852 A1 WO 2010099852A1
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- QZBJYTDDWVXFDF-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)arsane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[As](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QZBJYTDDWVXFDF-UHFFFAOYSA-N 0.000 description 1
- FQLSDFNKTNBQLC-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)phosphane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1P(C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F FQLSDFNKTNBQLC-UHFFFAOYSA-N 0.000 description 1
- QYWFCUVQKBNIRJ-UHFFFAOYSA-N tris(2,3,4,5,6-pentafluorophenyl)stibane Chemical compound FC1=C(F)C(F)=C(F)C(F)=C1[Sb](C=1C(=C(F)C(F)=C(F)C=1F)F)C1=C(F)C(F)=C(F)C(F)=C1F QYWFCUVQKBNIRJ-UHFFFAOYSA-N 0.000 description 1
- NZJQTVDLVPHKGY-UHFFFAOYSA-N tritert-butylstibane Chemical compound CC(C)(C)[Sb](C(C)(C)C)C(C)(C)C NZJQTVDLVPHKGY-UHFFFAOYSA-N 0.000 description 1
- YGPLLMPPZRUGTJ-UHFFFAOYSA-N truxene Chemical compound C1C2=CC=CC=C2C(C2=C3C4=CC=CC=C4C2)=C1C1=C3CC2=CC=CC=C21 YGPLLMPPZRUGTJ-UHFFFAOYSA-N 0.000 description 1
- WFKWXMTUELFFGS-UHFFFAOYSA-N tungsten Chemical compound [W] WFKWXMTUELFFGS-UHFFFAOYSA-N 0.000 description 1
- 239000010937 tungsten Substances 0.000 description 1
- 238000002061 vacuum sublimation Methods 0.000 description 1
- 238000001947 vapour-phase growth Methods 0.000 description 1
- 125000000391 vinyl group Chemical group [H]C([*])=C([H])[H] 0.000 description 1
- 229910052726 zirconium Inorganic materials 0.000 description 1
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Definitions
- the present invention relates to an electronic device containing metal complexes of the formula I.
- the invention also relates to the metal complexes themselves, their use in an electronic device and a process for their preparation.
- the invention is further directed to the ligands and the use of the ligands for the preparation of the metal complexes of the invention.
- OLEDs organic electroluminescent devices
- OLEDs organic electroluminescent devices
- organometallic complexes which exhibit phosphorescence instead of fluorescence are increasingly being used as emitting materials (M.A. Baldo et al., Appl. Phys. Lett. 1999, 75, 4-6).
- organometallic compounds for quantum mechanical reasons, up to four times energy and power efficiency is possible using organometallic compounds as phosphorescence emitters. In general, however, there are still room for improvement in OLEDs that show triplet emission.
- triplet emitters are usually employed as iridium complexes with bidentate ligands which coordinate via C and N.
- An improvement of these OLEDs could be achieved by using metal complexes with polypodal ligands or cryptates, whereby the complexes have a higher thermal stability, leading to a higher life expectancy.
- duration of the OLEDs leads (WO 04/081017, WO 05/113563, WO 06/008069).
- further improvements of the complexes are desirable in order to use them in high-quality and durable electroluminescent devices, for example for television or computer monitors.
- Metal complexes are also used in other functions in organic electroluminescent devices, for example Alq 3 (tris (hydroxyquinolinate) aluminum) as electron transport material or BAIq (for example T. Tsuji et al., Journal of the Society of Information Display
- Zinc complexes are also used as triplet matrix materials (eg WO 09/062578, EP 652273). Even with these materials, further improvements are desirable for their use in high-quality electroluminescent devices.
- the object of the present invention is therefore to provide novel organic electroluminescent devices containing metal complexes.
- the metal complexes can be used as emitters, as matrix materials, as hole-blocking materials, as electron-transport materials or in other functions in the OLED. There is still room for improvement in the case of red, green and blue phosphorescent metal complexes, especially in the case of blue-phosphorescent metal complexes.
- Organic electroluminescent devices containing these complexes are therefore the subject of the present invention.
- Another object of the present invention are particularly suitable metal complexes which can be used in organic electroluminescent devices.
- the invention therefore provides an electronic device comprising a compound of general formula I.
- M is a metal
- Y is independently NR, O or S at each occurrence
- X is independently CR 1 or N at each occurrence
- Ring atoms each of which may be substituted by one or more radicals R 2 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 2 , or a combination of these systems, wherein two or more adjacent substituents R 1 can also form together a mono- or polycyclic, aliphatic or aromatic ring system;
- R 2 is in each occurrence independently of one another H, D, F or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which also one or more H atoms may be replaced by F; two or more substituents R 2 may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
- Each R 3 is independently H, D, an aliphatic hydrocarbon radical of 1 to 20 carbon atoms or an aromatic or a heteroaromatic ring system of 5 to 30 aromatic ring atoms, which may be substituted by one or more radicals R 1 ; or R 3 is a coordinating group wherein R 3 binds to the metal M via a charged or uncharged exocyclic or endocyclic donor atom D;
- part-ligands L and L together can ggeeggeebbeenneennffaallllss üübbeerr eeiinnee VVeerrkknnüüppffuunngg vviia R form with L 'and / or LL "" ,, 3, along a dentate or multi polypodal ligand;
- Ar is independently at each occurrence an aromatic or heteroaromatic ring system with 5 to 30 aromatic ring atoms which may be substituted with one or more non-aromatic radicals R 1 ;
- L represents a ligand, which is shown in formulas II, III and IV in the square bracket.
- indices n, m and o are chosen so that the coordination number on the metal M in total, depending on the metal, corresponds to the usual coordination number for this metal. For transition metals, this is usually the coordination number 4, 5 or 6, preferably 4 or 6, depending on the metal. It is generally known that metal coordination compounds depend on the metal coordination compounds
- An aryl group for the purposes of this invention contains 6 to 40 carbon atoms;
- a heteroaryl group contains 2 to 40 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.
- aryl group or heteroaryl group either a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine, thiophene, etc., or a fused aryl or heteroaryl group, for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc ., Understood.
- a simple aromatic cycle ie benzene
- a simple heteroaromatic cycle for example pyridine, pyrimidine, thiophene, etc.
- a fused aryl or heteroaryl group for example naphthalene, anthracene, phenanthrene, quinoline, isoquinoline, etc .
- a cyclic carbene in the sense of this invention is a cyclic group which binds to the metal via a neutral carbon atom.
- the cyclic group may be saturated or unsaturated.
- Arduengo carbenes ie those carbenes, in which two nitrogen atoms are bonded to the carbene C atom, are preferred here.
- a five-membered arduengo carbene or another unsaturated five-membered carbene is also regarded as an aryl group in the context of this invention.
- 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 1 to 59 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.
- N or O atom can be connected.
- 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.
- Aromatic or heteroaromatic ring system with 5-60 aromatic ring atoms which may be substituted in each case with the abovementioned radicals R 1 to R 3 and which via any Aromatic or heteroaromatic positions can be linked, are understood in particular groups derived from benzene, naphthalene, anthracene, phenanthrene, Benzanthracen, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzopyrene, biphenyl, biphenylene, terphenyl, terphenylene , Fluorene, spirobifluorene,
- an alkyl group having 1 to 40 C atoms or a C 1 to C 40 alkyl group in which individual H atoms or Chh groups can be substituted by the abovementioned groups, for example the radicals methyl , Ethyl, n -propyl, i -propyl, n -butyl, i -butyl, s -butyl, t -butyl, 2-methylbutyl, n -pentyl, s -pentyl, tert -pentyl, 2-pentyl, neo -pentyl , Cyclopentyl, n-hexyl, s -hexyl, tert-hexyl, 2-hexyl, 3-hexyl, neo-hexyl, cyclohexyl, 2-methylpentyl, n-heptyl, 2-heptyl,
- an alkenyl group in the sense of
- the present invention includes ethenyl, propenyl, butenyl, pentenyl, cyclopentenyl, hexenyl, cyclohexenyl, heptenyl, cycloheptenyl, octenyl and cyclooctenyl.
- an alkynyl group is understood as meaning, for example, ethynyl, propynyl, butynyl, pentynyl, hexynyl, heptynyl and octynyl.
- methoxy, trifluoromethoxy, ethoxy, n-propoxy, i-propoxy, n-butoxy, i-butoxy, s-butoxy, t-butoxy are among a C 1 to C 40 alkoxy group or an alkoxy group of 1 to 40 carbon atoms or 2-methylbutoxy understood.
- a donor atom is understood to mean an atom which has at least one free electron pair and is therefore capable of binding to a metal atom or metal ion.
- the donor atom can be neutral or negative or positively charged.
- the donor atom is neutral or negatively charged.
- neutral donor atoms are nitrogen, which in a heteroaromatic such.
- B. pyridine is attached or which is in the form of an imine, or carbon in the form of a carbene.
- anionic donor atoms are carbon which is part of an aromatic or heteroaromatic, such.
- an exocyclic donor atom D is understood as meaning a donor atom which is not part of a cyclic substituent R 3 or the cyclic group Cy 1, as defined below, but which is bonded as substituent to R 3 or Cy 1, respectively which has at least one free electron pair and is thereby able to bind to a metal atom.
- exocyclic donor atoms are oxygen in the form of a phenolate, sulfur in the form of a thiolate, nitrogen in the form of a nitrile, amine, imine, amide or imide, phosphorus in the form of a phosphine or phosphite or carbon in the form of an isonitrile or acetylide.
- substructure M (L) n corresponds to the formulas IIa, IIIa, IVa, IIb, IHb or IVb,
- Each D 1 is independently an endocyclic donor atom selected from the group consisting of B, C, N, O and S;
- D 2 is in each occurrence independently an exocyclic donor group selected from the group consisting of O, S, NR 1 , N (R 1 ) 2 , PR 1 , P (R 1 ) 2 , P (O) R 1 , P (O) (R 1 ) 2 , AsR 1 , As (R 1 ) 2 , As (O) R 1 , As (O) (R 1 ) 2 , SbR 1 , Sb (R 1 ) 2 , Sb (O ) R 1 , Sb (O) (R 1 ) 2 , BiR 1 , Bi (R 1 ) 2 , Bi (O) R 1 , Bi (O) (R 1 ) 2 , OR 1 , SR 1 , SeR 1 and TeR 1 ;
- X 1 is independently of each occurrence C or N;
- Cy1 is each occurrence independently of one another an aromatic or heteroaromatic group or an aromatic or heteroaromatic ring system having 5 to 30 ring atoms, wherein X 1 and D 1 in the aromatic or heteroaromatic group or the aromatic or heteroaromatic Ring system are included or D 2 is bound as an exocyclic group.
- D 1 each independently represent an endocyclic
- Donor atom selected from N, C, O or S.
- D 2 each occurrence independently of one another is an exocyclic donor group selected from O, S, NR 1 , N (R 1 ) 2) PR 1 , P (R 1 ) 2 , wherein R 1 has the meaning given above.
- R 3 in the formulas II, Ml or IV or Cy1 in the formulas IIa, IMa or IVa are selected from the following structures (1) to (24):
- X is independently CR 1 or N at each occurrence, R 1 is as defined above, the dotted line represents a bond to the nitrogen atom of the boron-nitrogen heterocycle and * represents the coordination site to the metal.
- Y in the compounds of the general formula II, III or IV is NR 3 .
- metal M should preferably be understood a transition metal or a main group metal.
- M is a transition metal selected from Zr, Hf, Mo, W, Re, Ru 1 Os 1 Rh, Ir, Pd, Pt, Cu, Ag and Au. The metal can be present in different oxidation states.
- M is a main group metal selected from alkali metals (Li, Na, K, Rb, Cs), alkaline earth metals (Be, Mg, Ca, Sr, Ba), Al, Sn, Ge, Bi and Te.
- a plurality of ligands L can be connected to one another by a group Z.
- the substructure M (L) n is selected from the following structures (25) to (30):
- the pyridine ring may each be substituted by one or more radicals R 1 .
- the index n is chosen according to the coordination number of the metal M and as a function of the presence of further ligands L 'and L ", where Z is any bridging unit, since Z is the linkage of the ligands, but Z is the electronic Properties of the complex plays only a minor role, the exact structure of Z is not important.
- Z is preferably B, B (R 1 ) “ , B (C (R 1 ) 2 ) 3 , (R 1 ) B (C (R 1 ) 2 ) 3 " ⁇ B (O) 3 , (R 1 ) B (O) 3 -, B (C (R 1 ) 2 C (R 1 ) 2 ) 3l (R 1 ) B (C (R 1 ) 2 C (R 1 ) 2 ) 3 - , B (C (R 1 J 2 O) 3 , (R 1 ) B (C (R 1 ) 2 O) 3 -, B (OC (R 1 ) 2 ) 3 , (R 1 ) B (OC (R 1 ) 2 ) 3 -, C (R 1 ), CO " , CN (R 1 ) 2 , (R 1 ) C (C (R 1 ) 2 ) 3 , (R 1 ) C (O) 3) (R 1 ) C (C (R 1 ) 2 C (
- bridging unit Z is present in the molecule, in particular two bridging units Z. If more than one bridging unit Z is present in the molecule, these groups Z may be the same or different. Thus, the formation of macrocyclic ligands or cryptands is possible with two bridging units Z.
- L 'and / or L are neutral, monoanionic, dianionic or trianionic ligands, preferably neutral or monoanionic ligands L' and / or L" may be monodentate, bidentate, tridentate, tetradentate or pentadentate ligands.
- the compound of the general formula I may contain four monodentate ligands or two bidentate ligands or one tridentate and one monodentate ligand or a tetradentate ligand.
- the compound of general formula I may contain six monodentate ligands or three bidentate ligands or two tridentate ligands or one hexadentate ligand. Also, combinations of mono-, bi-, tri-, tetra- and pentadentate ligands are possible, provided that the coordination number on the metal gives six.
- the metal M in the compound of general formula I is sixfold coordinated and contains two bidentate ligands L.
- the compound of general formula I can thus each two monodentate ligands U and L ", or a bidentate Ligands L 'or L "included.
- L 'or L " is preferably a cyclometalated ligand or a ligand which binds via two oxygen atoms, in particular a ketoketonate derivative, preferably acetylacetonate, or a ligand which binds via oxygen and nitrogen, preferably picolinate.
- the metal M in the compound of general formula I is square-planar or tetrahedrally coordinated and preferably contains a bidentate
- the compound of general formula I may each contain a monodentate ligand L 'and L "or a bidentate ligand L', preferably a bidentate ligand
- the ligand L 'or L" is preferably a cyclometalated ligand Ligand which binds via two oxygen atoms, in particular a ketoketonate derivative, preferably acetylacetonate, or a ligand, which binds via oxygen and nitrogen, preferably picolinate.
- a monodentate ligand L and a tridentate ligand L 'or a tridentate ligand L and a monodentate ligand U are also possible.
- Preferred neutral, monodentate ligands L 'and L are each independently selected at each occurrence from carbon monoxide, NO, isonitriles, such as, for example, tert-butyl isonitrile, cyclohexyl isonitrile, adamantyl isonitrile, phenyl isonitrile, mesitylisonitrile, 2,6- Dimethylphenylisonitrile, 2,6-diisopropylphenylisonitrile, 2,6-di-tert-butylphenylisonitrile, amines, such as, for example, trimethylamine, triethylamine, morpholine, phosphines, such as, for example, trifluorophosphine, trimethylphosphine, tricyclohexylphosphine, Tri-te / f-butylphosphine, triphenylphosphine, tris (pentafluorophenyl)
- Preferred monoanionic monodentate ligands L 'and L " are each independently selected at each occurrence from hydride, deuteride, the halides F, Cl, Br and I, alkylacetylidene, such as, for example, methylC ⁇ C " , tert-butyl -C ⁇ C ⁇ , aryl and heteroaryl acetylidene, such as.
- cyanide, cyanate, isocyanate, thiocyanate, isothiocyanate, aliphatic or aromatic alcoholates such as, for example, methanolate, ethanolate, propanolate, / so-propanolate, te / f-butylate, phenolate, aliphatic or aromatic thioalcoholates, such as methanethiolate, ethanethiolate, propanethiolate, so-propanethiolate, tert-thiobutylate, thiophenolate, amides, such as, for example, dimethylamide, diethylamide, di- / so-propylamide, morpholide,
- Carboxylates such as. As acetate, trifluoroacetate, propionate, benzoate, and anionic, nitrogen-containing heterocycles, such as pyrrolidone, imidazolide, pyrazolide.
- the alkyl groups in these groups are preferably C 1 -C 20 -alkyl groups, more preferably C 1 -C 10 -alkyl groups, very particularly preferably C 1 -C 4 -alkyl groups.
- These groups and the aryl and heteroaryl groups are as defined above.
- Preferred neutral or mono- or dianionic bidentate or higher-dentate ligands L 'and L are each independently selected at each occurrence from diamines such as ethylenediamine, NNN'.N'-tetramethylethylenediamine, propylenediamine, N, N , N ', N'-tetramethylpropylenediamine, cis- or trans -diaminocyclohexane, cis- or trans -NNN'.N'-tetramethyldiaminocyclohexane, imines, such as, for example, 2- [1- (phenyl-imino) ethyl ] pyridine, 2- [1- (2-methylphenylimino) ethyl] pyridine, 2- [1- (2,6-di- / so-propylphenylimino) ethyl] pyridine, 2- [1- (methylimino) ethyl] pyridine
- bis-diphenylphosphinomethane bis-diphenylphosphinoethane, bis (diphenylphosphino) propane, bis (dimethylphosphino) methane, bis (dimethylphosphino) ethane, bis (dimethylphosphino) propane, bis (diethylphosphino) methane, bis (diethylphosphino) ethane, bis (diethylphosphino) propane, bis (di-Fe / t-butylphosphino) methane, bis (di- ferf-butylphosphino) ethane, bis (FeAf-butylphosphino) propane, 1, 3-diketonates derived from 1, 3-diketones, such as , Acetylacetone, benzoylacetone, 1,5-diphenylacetylacetone,
- ethyl acetoacetate carboxylates derived from aminocarboxylic acids, such as.
- pyridine-2-carboxylic acid quinoline-2-carboxylic acid, glycine, N, N-dimethyl-glycine, alanine, N, N-dimethylaminoalanine, salicyliminates derived from salicylimines, such as. Methylsalicylimine, ethylsalicylimine, phenylsalicylic imine, dialcoholates derived from dialcohols, such as.
- ethylene glycol, 1, 3-propylene glycol and dithiolates derived from dithiols, such as. B. 1, 2-ethylenedithiol, 1, 3-propylenedithiol.
- Heterocycles such as.
- tetrakis (1-imidazolyl) borate and tetrakis (1-pyrazolyl) borate For example, tetrakis (1-imidazolyl) borate and tetrakis (1-pyrazolyl) borate.
- ligand L 1 and L "for compounds according to formula I are known, and it can, without inventive step further select such ligands as ligand L 1 and L "for compounds according to formula I.
- it is particularly suitable for the combination of two groups, as shown above by the formulas (1) to (24), wherein one group preferably binds via a neutral nitrogen atom or a carbene atom and the other group preferably via a negatively charged carbon atom or a negatively charged nitrogen atom binds.
- the ligand U or L can then be formed from the groups of formulas (1) to (24) by these groups each bind to each other at the position indicated by a dashed bond and bind to the metal at the positions marked with *.
- ligands L 'or L are ⁇ 5 -cyclopentadienyl, ⁇ 5 -
- Pentamethylcyclopentadienyl, ⁇ 6 -benzene or ⁇ 7 -cycloheptatrienyl which may each be substituted by one or more radicals R 1 .
- ligands L 'or L are 1,3,5-cis-cyclohexane derivatives, in particular of the formula (44), 1,1,1-tri (methylene) methane derivatives, in particular of the formula (45) and 1,1,1-trisubstituted methanes, in particular of the formula (46),
- R 1 has the abovementioned meaning and A, identical or different at each occurrence O “ , S “ , COO “ , P (R 1 ) 2 or N (R 1 ) 2 means.
- the complexes of the formula I can in principle be prepared by various processes, but the processes described below have proven to be particularly suitable.
- the complexes according to formula I are obtained by reacting the ligand according to formula V, VI or VII and optionally further ligands L ', L "with metal alcoholates of formula (47), with metal ketoketones according to formula (48) or metal halides according to formula (49) .
- Hal is the same or different at each occurrence, F, Cl, Br or I;
- Lig is the same or different at each occurrence as a neutral or monoanionic, monodentate or bidentate ligand, for example a halide, hydroxide or ethylene glycolate;
- q is the same or different at each occurrence 0, 1, 2, 3 or 4, preferably 0, 1 or 2;
- r is the same or different 1, 2, 3, 4, 5 or 6 at each occurrence.
- the compound of formula (48) and (49) may also be charged and contain one or more counterions; Furthermore, the compounds of the formulas (47) to (49), in particular of the formula (49), can also be present as hydrate.
- a complex-analogous synthesis of the ligands is possible by reacting precursors of the ligand with metal compounds of the formula (47), (48) or (49) and reacting the precursors of the ligand on the metal complex thus formed to form the finished ligand.
- This may be advantageous in particular for tetradentate or hexadentate ligand systems by introducing the bridging unit Z to the complex.
- the synthesis can be activated, for example thermally, photochemically and / or by microwave radiation.
- the complexes can be easily obtained in high purity, preferably in a purity of> 99% by 1 H-NMR or HPLC analysis, more preferably> 99.9%.
- Examples of preferred structures are the structures (1) to (362) listed in the following table.
- O-FETs organic thin-film transistors
- O-LETs organic light-emitting transistors
- O-ICs organic integrated circuits
- O-SCs organic solar cells
- O-FQDs organic field quench Devices
- LECs light-emitting electrochemical cells
- O-lasers organic laser diodes
- Active components are generally the organic, organometallic or inorganic materials incorporated between the anode and cathode, for example, charge injection, charge transport or charge blocking materials, but especially emission materials and matrix materials.
- the compounds according to the invention exhibit particularly good properties, in particular as emission material in organic electroluminescent devices, as will be explained in more detail below.
- a preferred embodiment of the invention are therefore organic electroluminescent devices.
- the organic electroluminescent device preferably contains cathode, anode and at least one emitting layer, wherein the compound of general formula I is preferably present as an emitting compound in the emitting layer or wherein the compound of general formula I is present as a matrix material for an emitting compound in the emitting layer, particularly preferred as the emitting compound.
- the organic electronic device may contain further layers selected from in each case one or more hole injection layers, hole transport layers, hole blocking layers, electron transport layers, electron injection layers, electron blocking layers. layers, exciton blocking layers, charge generation layers and / or organic or inorganic p / n junctions.
- intermediate layers may be introduced between two emitting layers or else between other layers, which have, for example, an exciton-blocking function. It should be noted, however, that not necessarily each of these layers must be present.
- 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. If multiple emission layers are present, they preferably have a total of several emission maxima between 380 nm and 750 nm, so that overall white emission results, ie. H.
- various emitting compounds are used which can fluoresce or phosphoresce. Particular preference is given to three-layer systems, the three layers exhibiting blue, green and orange or red emission (for the basic structure see, for example, WO 05/011013).
- the electronic device contains the compound according to formula I or the preferred embodiments listed above as an emitting compound in an emitting layer.
- the compound according to formula I When the compound according to formula I is used as the emitting compound in an emitting layer, it is preferably used in combination with one or more matrix materials.
- the mixture of the compound according to formula I and the matrix material contains between 1 and 99% by volume, preferably between 2 and
- the mixture contains between 99 and 1% by volume, preferably between 98 and 10% by volume, particularly preferably between 97 and 60% by volume, in particular between 95 and 85% by volume of the matrix material based on the total mixture of emitter and matrix material.
- Suitable matrix materials for the compounds according to the invention are ketones, phosphine oxides, sulfoxides and sulfones, for. B. according to
- WO 07/063754 or WO 08/056746 or zinc complexes, e.g. For example EP 652273 or WO 09/062578.
- Further suitable matrix materials are the compounds according to the formula I of the present application, as explained in more detail below. In general, all matrix materials used according to the prior art for phosphorescent emitters in organic electroluminescent devices can also be used for the compounds according to the invention. It is also possible to use mixtures of these matrix materials.
- the organic electroluminescent device does not contain a separate hole transporting layer or that it contains as the hole transporting material in the hole transporting layer a metal complex which is the same or similar to the complex used in the emitting layer.
- the compound according to formula I or the preferred embodiments listed above is used as matrix material for an emitting compound in an emitting layer.
- the electroluminescent device according to the invention contains in the emitting layer a matrix material and furthermore at least two phosphorescent emitters, wherein at least one of the two phosphorescent emitters is a compound of the abovementioned formula (I).
- the phosphorescent emitter which emits shorter wavelength, serves as a matrix for the phosphorescent emitter, which emits a longer wavelength.
- the compound according to formula (I) can be the shorter-wavelength emitter compound or the longer-wavelength emissive compound. Likewise, both phosphorescent compounds
- the compound according to formula I or the above-mentioned preferred embodiments is used as the matrix material for an emitting compound in an emitting layer, it is preferably used in combination with one or more phosphorescent materials (triplet emitters) or fluorescent materials (singlet emitters).
- Preferred emissive materials are phosphorescent materials.
- phosphorescence is understood as meaning the luminescence from an excited state with a higher spin multiplicity, ie a spin state> 1, in particular from an excited triplet state or from an MLCT mixed state.
- all luminescent transition metal complexes in particular all luminescent iridium, platinum and copper compounds, are regarded as phosphorescent materials.
- the mixture of the compound according to formula I or the above-mentioned preferred embodiment and the emitting compound then contains between 99 and 1% by volume, preferably between 98 and 10% by volume, particularly preferably between 97 and 60% by volume. , in particular between 95 and 85% by volume of the compound according to formula I or the above-mentioned preferred embodiment based on the total mixture of emitter and matrix material. Accordingly, the mixture contains between 1 and 99% by volume, preferably between 2 and 90% by volume, more preferably between 3 and 40% by volume, in particular between 5 and 15% by volume of Emitters based on the total mixture of emitter and matrix material. It is also possible to use a compound of formula (I) and another compound together as a matrix material.
- Preferred phosphorescence emitters are compounds which are copper,
- Molybdenum tungsten, rhenium, ruthenium, osmium, rhodium, iridium, palladium, platinum, silver, gold or europium, especially compounds containing iridium or platinum.
- WO 00/70655 WO 01/41512, WO 02/02714, WO 02/15645, EP 1191613, EP 1191612, EP 1191614, WO 05/033244 or WO 09/118087.
- Further suitable emitters are the abovementioned compounds of the formula I or the abovementioned preferred embodiments.
- all phosphorescent complexes used in the prior art for phosphorescent OLEDs and as known to those skilled in the art of organic electroluminescence are suitable, and those skilled in the art may use other phosphorescent complexes without inventive step.
- the compound according to formula I or the preferred embodiments listed above is used as a hole-blocking material in a hole-blocking layer and / or as an electron-transport material in an electron-transport layer.
- the emitting layer may be fluorescent or phosphorescent.
- organic electroluminescent device characterized in that one or more layers with a
- Sublimation method be applied.
- the materials in vacuum sublimation are at an initial pressure of usually less than 10 -5 mbar, preferably below 10 "vapor-deposited 6 mbar. However, it is also possible that the initial pressure is even lower, for example less than 10" 7 mbar.
- an organic electroluminescent device characterized in that one or more layers are applied 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
- 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, offset printing, LITI (Light Induced Thermal Imaging, thermal transfer printing), ink-jet printing (ink jet printing) or Nozzle Printing, are produced.
- soluble compounds are necessary, which are obtained for example by suitable substitution.
- Layers of solution are applied and one or more other layers are evaporated.
- M is a metal
- Y is independently NR 3 , O or S at each occurrence
- X is independently CR 1 or N at each occurrence
- R 2 is in each occurrence independently of one another H, D, F or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 C atoms, in which also one or more H atoms may be replaced by F; two or more substituents R 2 may also together form a mono- or polycyclic, aliphatic or aromatic ring system;
- R 3 is each occurrence independently of one another aliphatic hydrocarbon radical having 1 to 20 carbon atoms or an aromatic or a heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by R 1 , characterized in that at least one radical R 3 is a coordinating group which has a charged or uncharged exocylisches endo- or cyclic D donor atom that binds to the metal M;
- part-ligands L and L together can ggeeggeebbeenneennffaallllss üübbeerr eeiinnee VVeerrkknnüüppffuunngg vviia R form with L 'and / or LL "" ,, 3, along a dentate or multi polypodal ligand;
- Ar at each occurrence is independently an aromatic or heteroaromatic ring system having from 5 to 30 aromatic ring atoms which may be substituted with one or more non-aromatic radicals R 1 ;
- Coordination number 4 has.
- each R 3 independently represents an aromatic or a heteroaromatic ring system having 5 to 30 aromatic ring atoms, in which one or more H atoms may be replaced by R 1 , wherein at least one group R 3 has a charged or uncharged exocyclic or endocyclic donor atom D that binds to metal M; several partial ligands L or L together with L 'and / or L ", optionally together via a linkage via R 3 , form a polydentate or polypodal ligand R 3 is particularly preferably selected from structures of the formulas (1) to (24 )
- Yet another object of the present invention is a process for preparing the compounds of formula I by reacting the corresponding free ligand of the formula V, VI or VII with metal compounds of the above formulas (47), (48) or (49).
- the compounds of the general formula I according to the invention can be used as emitter compound, as matrix material, as hole-blocking material and / or as electron-transport material in an electronic system
- ligands L which are a valuable intermediate for the synthesis of the metal complexes of the invention.
- the invention thus relates to a ligand L of the general formula V 1 VI or VII
- R 1 R 3 and Y have the meanings mentioned above for the protection of substances, in particular the abovementioned preferred embodiments, and furthermore:
- R 4 is H or halogen
- the ligand L corresponds to the formulas Va, VIa, VIIa, Vb, VIb or VIIb,
- the donor atom D 1 is preferably selected from B, C, N, O and S and the donor group D 2 is preferably selected from O, S, NR 1 , N (R 1 ) 2 , PR 1 and P (R 1 ) 2 .
- Y NR 3 .
- Preferred structures R 3 or Cy 1 of the ligand L are selected from the following structures (1) to (24):
- X is independently CR 1 or N 30 each occurrence, R 1 is as defined above and the dotted line represents a bond to the nitrogen atom of the boron-nitrogen heterocycle.
- Particularly preferred ligands L are selected from the following structures: 35
- the ligand L serves as an intermediate for the preparation of the metal complexes of the general formula I.
- the invention thus also relates to the use of the ligand L of the general formula V, VI or VII
- the ligand corresponds to the abovementioned formulas Va, VIa, VIIa, Vb, VIb or VIIb.
- Y NR.
- Preferred structures R 3 or Cy1 of the ligand L are selected from the structures (1) to (24) listed above.
- Particularly preferred ligands L are the structures (50) to (55) listed above.
- the compounds according to the invention of the formula (I) described above in particular compounds which are substituted by reactive leaving groups such as bromine, iodine, boronic acid or boronic acid esters, can be used as monomers for producing corresponding oligomers, dendrimers or polymers.
- the oligomerization or polymerization is preferably carried out via the halogen functionality or the boronic acid functionality.
- Another object of the invention are therefore oligomers, polymers or dendrimers containing one or more compounds of formula I, wherein one or more bonds of the complex of formula I 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 monomers according to the invention are homopolymerized or copolymerized with further monomers.
- 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 US Pat WO 05/014689), cis-and trans-indeno-fluorenes (for example according to WO 04/041901 or WO 04/113412), ketones (for example according to WO 05/040302), phenanthrenes (eg. according to fluorenes (for example according to EP 842208 or WO 00/22026), spirobifluorenes (for example according
- WO 05/104264 or WO 07/017066 or also several of these units.
- 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 further units, for example hole transport units, in particular those based on triarylamines, and / or electron transport units.
- the metal complexes according to the invention can also be further functionalized and thus converted into extended metal complexes.
- the functionalization with arylboronic acids according to SUZUKI or with primary or secondary amines according to HARTWIG-BUCHWALD can be mentioned here.
- the electronic devices according to the invention are distinguished by the following surprising advantages over the prior art:
- the compounds of the present invention have high thermal stability.
- Organic electroluminescent devices containing compounds according to formula I as emitting materials have an excellent lifetime.
- Blue phosphorescent complexes are available which have good color coordinates and a long lifetime when used in organic electroluminescent devices. This is a significant advance over the prior art, since so far blue phosphorescent devices usually only with bad Color coordinates and in particular a poor life were accessible.
- Precursors 1-4 Synthesis of symmetrical ⁇ /, ⁇ / -substituted o-phenylenediamines
- N 1 N-substituted o-phenylenediamines are prepared from o-dibromobenzene and a corresponding amine analogously to Tetrahedron Letters 2004, 45, 6851-6853.
- Precursors 5-12 Synthesis of unsymmetrical N, N-substituted o-phenylenediamines
- the 2-bromo-1,3,2-diazaborolidines listed below are prepared from the corresponding diamines by reaction with a boron tribromide-triethylamine adduct analogously to Organometallics 2005, 24, 5455-5463.
- compound 16 is prepared from di- ⁇ -chlorotetrakis [2- (2-pyridinyl) -phenyl-C, N] -diiridium and 2-bromo-1-phenyl-3-pyridin-2-yl-benzo [1, 3, 2] diazaborole shown.
- compounds 17-18 are prepared from corresponding 2-bromobenzo [1,2,2] diazaboroles and bis (benzonitrile) -platindichloride.
- Example 20 Preparation and characterization of organic electroluminescent devices
- 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 (or matrix) M bis [1, 3 ', 1 I , 1 ", 3", 1 "', 3 II ', 1 "”] quinquephenyl-5 "-ylmethanone (according to DE102008033943.1, Example 3) and the guest material (dopant) 10% fac-tris [2- (2-pyridinyl) (5-cyanophenyl)] iridium (III) (TEB) for a blue emission.
- OLEDs with identical structure and dopants according to the invention are described. Analogously to the above-mentioned general method, OLEDs are produced with the following structure:
- HIL Hole Injection Layer
- HTL hole transport layer
- EBL Electron blocking layer
- EBL 15 nm EBL (9,9-bis- (3,5-diphenylamino-phenyl) fluorene
- EBL, M and TEB are shown below for the sake of clarity.
- the above-described compounds 1-19 are used.
- OLEDs are characterized by default; For this, the electroluminescence spectra, the external quantum efficiency (measured in%) as a function of the brightness, calculated from current-voltage-brightness characteristics (IUL characteristics), and the service life are determined.
Abstract
Description
Claims
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JP2011552336A JP5666483B2 (ja) | 2009-03-02 | 2010-02-03 | アザボロール配位子を有する金属錯体及び当該錯体を有する電子デバイス |
KR1020117023019A KR101842719B1 (ko) | 2009-03-02 | 2010-02-03 | 아자보롤 리간드를 갖는 금속 착물 및 그를 갖는 전자 소자 |
DE112010000948T DE112010000948A5 (de) | 2009-03-02 | 2010-02-03 | Metallkomplexe mit Azaborol-Liganden und elektronische Vorrichtung damit |
US13/254,220 US9074128B2 (en) | 2009-03-02 | 2010-02-03 | Metal complexes having azaborol ligands and electronic device having the same |
CN201080007829.4A CN102317407B (zh) | 2009-03-02 | 2010-02-03 | 含有氮杂硼杂环戊烯配体的金属络合物和含有该金属络合物的电子器件 |
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WO2012069121A1 (de) | 2010-11-24 | 2012-05-31 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
WO2012136295A1 (de) | 2011-04-05 | 2012-10-11 | Merck Patent Gmbh | Organische elektrolumineszenzvorrichtung |
WO2012143080A2 (de) | 2011-04-18 | 2012-10-26 | Merck Patent Gmbh | Materialien für organische elektrolumineszenzvorrichtungen |
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Also Published As
Publication number | Publication date |
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CN102317407A (zh) | 2012-01-11 |
JP2012519384A (ja) | 2012-08-23 |
DE112010000948A5 (de) | 2012-07-19 |
US9074128B2 (en) | 2015-07-07 |
TW201100439A (en) | 2011-01-01 |
KR20110133583A (ko) | 2011-12-13 |
CN102317407B (zh) | 2014-12-31 |
KR101842719B1 (ko) | 2018-03-27 |
DE102009011223A1 (de) | 2010-09-23 |
TWI568741B (zh) | 2017-02-01 |
US20120004407A1 (en) | 2012-01-05 |
JP5666483B2 (ja) | 2015-02-12 |
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