US20080018221A1 - Use Of Transition Metal Carbene Complexes In Organic Light-Emitting Diodes (Oleds) - Google Patents

Use Of Transition Metal Carbene Complexes In Organic Light-Emitting Diodes (Oleds) Download PDF

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US20080018221A1
US20080018221A1 US11/720,291 US72029105A US2008018221A1 US 20080018221 A1 US20080018221 A1 US 20080018221A1 US 72029105 A US72029105 A US 72029105A US 2008018221 A1 US2008018221 A1 US 2008018221A1
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carbene
ligands
transition metal
complexes
group
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Martina Egen
Klaus Kahle
Markus Bold
Thomas Gessner
Christian Lennartz
Simon Nord
Hans-Werner Schmidt
Mukundan Thelakkat
Markus Bate
Chritian Neuber
Wolfgang Kowalsky
Christian Schildknecht
Hans-Hermann Johannes
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BASF SE
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Definitions

  • the present invention relates to the use of transition metal-carbene complexes in organic light-emitting diodes (OLEDs), to a light-emitting layer, to a blocking layer for electrons or excitons, or to a blocking layer for holes, each comprising these transition metal-carbene complexes, to OLEDs comprising these transition metal-carbene complexes, to devices which comprise an inventive OLED, and to transition metal-carbene complexes.
  • OLEDs organic light-emitting diodes
  • OLEDs organic light-emitting diodes
  • OLEDs organic light-emitting diodes
  • cathode ray tubes and liquid-crystal displays for the production of flat visual display units.
  • devices comprising OLEDs are suitable especially for mobile applications, for example for applications in mobile telephones, laptops, etc.
  • WO 02/15645 relates to OLEDs which have a light-emitting layer which comprises phosphorescent transition metal compounds.
  • the transition metal compounds exhibit electrophosphorescence, especially in the blue region of the visible electromagnetic spectrum.
  • the color coordinates of the blue emitted by the complexes disclosed in WO 02/15645 are in need of improvement.
  • WO 01/41512 relates to OLEDs which have a light-emitting layer which comprises a molecule of the general formula L 2 MX where M is more preferably iridium and L is selected from the group consisting of 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenylbenzothiazole, 7,8-benzoquinoline, coumarin, thienylpyridine, phenylpyridine, benzothienylpyridine, 3-methoxy-2-phenylpyridine and tolylpyridine, and X is selected from the group consisting of acetylacetonate, hexafluoroacetylacetonate, salicylidenes, picolinate and 8-hydroxyquinolinate.
  • M is more preferably iridium
  • L is selected from the group consisting of 2-(1-naphthyl)benzoxazole, 2-phenylbenzoxazole, 2-phenyl
  • WO 00/70655 relates to electroluminescent layers which have, as the light-emitting substance, a phosphorescent organometallic iridium compound or osmium compound. Preference is given to using tris(2-phenylpyridine)iridium as the light-emitting compound.
  • Electroluminescence refers both to electrofluorescence and to electrophosphorescence.
  • the provision of further compounds for use as materials which block electrons, excitons or holes is of interest.
  • the transition metal complexes of the formula I may be used in any layer of an OLED, and the ligand skeleton or central metal may be varied for adjustment to desired properties of the metal complexes.
  • the transition metal complexes of the formula I in a blocking layer for electrons, a blocking layer for excitons, a blocking layer for holes, a hole-transporting layer, an electron-transporting layer or the light-emitting layer of the OLED.
  • Preference is given to using the compounds of the formula I as emitter molecules in OLEDs.
  • a bidentate ligand means a ligand which is coordinated at two sites to the transition metal atom M.
  • a monodentate ligand refers to a ligand which coordinates at one site on the ligand to the transition metal atom M.
  • octahedral complexes for example Ir(III) complexes
  • both cis/trans isomers when the complexes are of the general composition MA 2 B 4 and fac-mer isomers (facial/meridional isomers) when the complexes are of the general composition MA 3 B 3 are possible.
  • cis/trans isomers are possible when the complexes are of the general composition MA 2 B 2 .
  • the variables A and B are each a binding site of a ligand, and not only monodentate, but also bidentate ligands may be present.
  • An unsymmetric bidentate ligand has, according to the abovementioned general composition, one A group and one B group, a symmetric ligand two A groups or two B groups.
  • cis/trans and fac-mer isomers In octahedral complexes, cis isomerism means that the two A groups in complexes of the composition MA 2 B 4 occupy adjacent corners of an octahedron, while the two A groups in transisomerism occupy mutually opposite corners of an octahedron.
  • three groups of the same type may either occupy the corners of one octahedral face (facial isomer) or a meridian, i.e. two of the three ligand binding sites are trans to one another (meridional isomer).
  • cisisomerism means that, in complexes of the composition MA 2 B 2 , both the two A groups and the two B groups occupy adjacent corners of a square, while both A groups and both B groups in the case of trans isomerism each occupy the two diagonally opposite corners of a square.
  • cis/trans isomers in square planar metal complexes see, for example, J. Huheey, E. Keiter, R. Keiter, Anorganische Chemie: Prinzipien von Struktur und Reeducationmaschine, 2nd, newly revised edition, translated into German and extended by Ralf Steudel, Berlin; New York: de Gruyter, 1995, pages 557 to 559.
  • the carbene ligand may also be bonded to the metal center in accordance with the formula shown below provided that the group comprises a CH bond which is suitable for cyclometalation and is adjacent to the double bond.
  • the group comprises a CH bond which is suitable for cyclometalation and is adjacent to the double bond.
  • one carbene ligand may have the bond to the metal center M shown above and the at least one further carbene ligand may have the bond to the metal center M shown in formula I.
  • the different isomers of the metal complexes of the formula I may be purified and/or separated by processes known to those skilled in the art, for example by chromatography, sublimation or crystallization.
  • the present invention therefore relates both to individual isomers of the transition metal-carbene complexes of the formula I and to mixtures of different isomers in any mixing ratio.
  • Transition metal complexes which comprise carbene ligands are known in the prior art. For instance, apamann et al., J. Am. Chem. Soc., 2002, 124, 10473 to 10481 and Danapoulos et al., J. Chem. Soc., Dalton Trans., 2002, 3090 to 3091 relate to iridium complexes which comprise a carbene ligand having the following structural unit
  • U.S. Pat. No. 6,160,267 and U.S. Pat. No. 6,338,977 relate to a molecular light-emitting diode which changes its color depending on vapors surrounding it.
  • This electrode has a sensor-emitter layer which comprises a neutral platinum complex, in which platinum is coordinated by two negatively charged ligands selected from the group consisting of CN ⁇ , NO 2 ⁇ , NCO ⁇ , NCS ⁇ , Cl ⁇ , Br ⁇ , I ⁇ and oxalate, and the two further ligands are selected from at least one and at most two arylisonitrile groups and a Fischer carbene complex which has the formula ⁇ C(Y)—NH—C 6 H 4 -alkyl, where Y is O-alkyl, NH-alkyl or N(alkyl) 2 .
  • transition metal complexes of the formula I according to the present application in OLEDs especially as light-emitting substances in OLEDs, are suitable for the production of displays.
  • the transition metal-carbene complexes of the general formula I used in accordance with the invention preferably have a metal atom M selected from the group consisting of Rh, Ir, Pd, Pt, Ru and Os, preference being given to Rh(III), Ir(III), Pd(II), Pt(II), Ru(III), Ru(IV) and Os(IV).
  • Metal atoms used with particular preference are Rh, Ir, Pt and Ru, preferably as Rh(III), Ir(III), Pt(II), Ru(III) and Ru(IV).
  • Ir or Pt as the metal atom M, preferably as Ir(III) or Pt(II), most preferably Ir(III).
  • Suitable mono- or dianionic ligands L preferably monoanionic ligands L, which may be mono- or bidentate are any ligands used customarily as mono- or bidentate, mono- or dianionic ligands.
  • Suitable monoanionic monodentate ligands are, for example, halides, in particular Cl ⁇ and Br ⁇ , pseudohalides, in particular CN ⁇ , cyclopentadienyl (Cp ⁇ ), alkyl radicals which are bonded via a sigma bond to the transition metal M, for example CH 3 , alkylaryl radicals which are bonded via a sigma bond to the transition metal M, for example benzyl.
  • Suitable monoanionic bidentate ligands are, for example, acetylacetonate and derivatives thereof, picolinate, Schiff bases, amino acids and tetrakis(1-pyrazolyl)borates, and the bidentate monoanionic ligands specified in WO 02/15645, of which preference is given to acetylacetonate and picolinate.
  • Suitable uncharged mono- or bidentate ligands have already been specified above.
  • Preferred uncharged monodentate ligands are selected from the group consisting of PPh 3 , P(OPh) 3 , AsPh 3 , CO, optionally substituted pyridines, nitrites and derivatives thereof.
  • Suitable uncharged mono- or bidentate ligands are preferably 1,4-diphenyl-1,3-butadiene, 1-phenyl-1,3-pentadiene, 2,4-hexadiene, cyclooctene, ⁇ 4 -cyclooctadiene and ⁇ 2 -cyclooctadiene (in each case 1,3 and 1,5) and also optionally substituted phenanthrolines.
  • n being at least 2, in which case the carbene ligands may be the same or different, and to m and q each being 0 or ⁇ 1, and the ligands L and K when m>1 or q>1 may each be the same or different.
  • the variables M, L, K, Do, r, Y 1 to Y 5 and A are each as already defined above.
  • transition metal-carbene complexes of the formula I used in accordance with the invention preference is also given to n being at least 2, in which case the carbene ligands may be the same or different, and to m and q each being 0.
  • the variables M, L, K, Do, r, Y 1 to Y 5 and A here too are each as already defined above.
  • transition metal-carbene complexes of the formula I used in accordance with the invention preference is given in the transition metal-carbene complexes of the formula I used in accordance with the invention to n being at least 2, and to the carbene ligands being the same and to m and q each being 0.
  • the variables M, L, K, Do, r, Y 1 to Y 5 and A are again each as already defined above.
  • the number n of carbene ligands in uncharged transition metal complexes is from 1 to 3, preferably 2 or 3, more preferably 3.
  • the carbene ligands may be the same or different, preferably the same.
  • the number m of monoanionic ligands L in the aforementioned case is accordingly 4, 2 or 0, preferably 2 or 0, more preferably 0.
  • the ligands L may be the same or different, preferably the same.
  • n of carbene ligands in transition metal complexes in which, for example, the transition metal atoms Pt(II) or Pd(II) have a coordination number of 4 is 1 or 2, preferably 2.
  • the carbene ligands may be the same or different, preferably the same.
  • the number m of monoanionic ligands L in the aforementioned case is accordingly 2 or 0, more preferably 0.
  • the ligands L may be the same or different, preferably the same.
  • the number q of uncharged ligands K is dependent upon whether the coordination number 6, for example for Ir(III), Rh(III) or Ru(III), or 4, for example for Pt(II) or Pd(II), has already been attained with the aid of the carbene ligands and the ligands L.
  • n 3
  • q assumes a value of 0.
  • Pt(II) or Pd(II) are used
  • n 2
  • q likewise assumes a value of 0.
  • aryl, heteroaryl, alkyl, alkenyl and alkynyl are each defined as follows:
  • Aryl is a radical having a basic skeleton of from 6 to 30 carbon atoms, preferably from 6 to 18 carbon atoms, which is formed from an aromatic ring or a plurality of fused aromatic rings.
  • Suitable basic skeletons are, for example, phenyl, naphthyl, anthracenyl or phenanthrenyl. This basic skeleton may be unsubstituted (i.e. that all carbon atoms which are substitutable bear hydrogen atoms), or be substituted at one of, a plurality of, or all, substitutable positions of the basic skeleton.
  • Suitable substituents are, for example, alkyl radicals, preferably alkyl radicals having from 1 to 8 carbon atoms, more preferably methyl, ethyl or isopropyl, aryl radicals, preferably C 6 -aryl radicals, which may in turn be substituted or unsubstituted, heteroaryl radicals, preferably heteroaryl radicals which comprise at least one nitrogen atom, more preferably pyridyl radicals, alkenyl radicals, preferably alkenyl radicals which bear one double bond, more preferably alkenyl radicals having one double bond and from 1 to 8 carbon atoms, or groups having donor or acceptor action.
  • Groups having donor action include groups which have a +I and/or +M effect, and groups having acceptor action include groups which have a ⁇ I and/or ⁇ M effect.
  • Suitable groups having donor or acceptor action are halogen radicals, preferably F, Cl, Br, more preferably F, alkoxy radicals, aryloxy radicals, carbonyl radicals, ester radicals, amine radicals, for example alkyl-, dialkyl-, aryl-, diarylamine radicals or else diarylamine radicals having bridged aryl radicals such as 1-carbazolyl, amide radicals, CH 2 F groups, CHF 2 groups, CF 3 groups, CN groups, thio groups or SCN groups.
  • aryl radicals When the aryl radicals are substituted, they most preferably bear substituents selected from the group consisting of methyl, F, Cl, aryloxy and alkoxy.
  • Aryl is preferably a C 6 -C 18 -aryl radical, more preferably a C 6 -aryl radical, which is optionally substituted by at least one of the aforementioned substituents.
  • the C 6 -C 18 -aryl radical preferably C 6 -aryl radical
  • Heteroaryl refers to radicals which differ from the above-specified aryl in that at least one carbon atom in the basic aryl skeleton has been replaced by a heteroatom.
  • Preferred heteroatoms are N, O and S.
  • one or two carbon atoms of the basic aryl skeleton have been replaced by heteroatoms.
  • the basic skeleton is selected from systems such as pyridine and five-membered heteroaromatics such as pyrrole or furan.
  • the basic skeleton may be substituted at one of, a plurality of, or all, substitutable positions of the basic skeleton. Suitable substituents are the same as have already been specified under the definition of aryl.
  • Alkyl refers to a radical having from 1 to 20 carbon atoms, preferably from 1 to 10 carbon atoms, more preferably from 1 to 8 carbon atoms.
  • the alkyl may be branched or unbranched and optionally be interrupted by one or more heteroatoms, preferably Si, N, O or S, more preferably N, O or S.
  • the alkyl may be substituted by one or more of the substituents specified under the definition of aryl. It is likewise possible that the alkyl bears one or more aryl groups. In this context, all of the above-listed aryl groups are suitable. More preferably, alkyl is selected from the group consisting of methyl, ethyl, n-propyl, isopropyl and tert-butyl.
  • Alkenyl refers to a radical which corresponds to the aforementioned alkyl having at least two carbon atoms, with the difference that at least one C—C single bond of the alkyl, where possible, has been replaced by a C—C double bond.
  • the alkenyl preferably has one or two double bonds.
  • Alkynyl accordingly refers to a radical which corresponds to the aforementioned alkyl having at least two carbon atoms, with the difference that at least one C—C single bond of the alkyl, where possible, has been replaced by a C—C triple bond.
  • the alkynyl preferably has one or two triple bonds.
  • Y 1 and Y 2 are each independently hydrogen, alkyl, aryl, heteroaryl or alkenyl.
  • Y 1 is preferably hydrogen.
  • Y 2 is preferably hydrogen or alkyl, more preferably hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • Y 1 and Y 2 together with the carbon atoms to which they are bonded, form a six-membered aromatic ring which may comprise one or two nitrogen atoms. This may be fused to a further, optionally fused and optionally heteroatom-comprising ring. In this case, the heteroatoms may be part of the ring or be bonded to the ring (in the “exo-position”).
  • Preferred substructures of the carbene ligands are:
  • Y 3 and Y 2 together with the donor atom Do and the carbon atom to which Y 2 is bonded, may form a five- or six-membered ring which, apart from the donor atom Do, may also comprise one further heteroatom selected from the group consisting of N, O and S.
  • Y 2 (together with Y 1 ) may already be part of an optionally (more highly) fused aromatic ring, for instance in the above-listed substructures of the carbene ligands, or Y 2 is a (formally) independent radical which, with Y 3 , forms a further substructure of the carbene ligands.
  • Preferred substructures are: where X is a CH 2 group or an oxygen atom.
  • Preferred substructures are: where the symbol is preferably as defined above and X is a CH 2 group or an oxygen atom.
  • variable A in formula I is a bridge having three or four atoms, of which one or two atoms may be heteroatoms and the remaining atoms are carbon atoms, so that the group (also referred to hereinbelow as “G”) forms a five- or six-membered heteroaromatic ring or a benzene ring.
  • Possible heteroatoms are in particular O, N and S.
  • Suitable five-membered heteroaromatic rings in the definition of the group G are listed below: where R is hydrogen, alkyl, alkenyl, alkynyl, aryl or heteroaryl, as defined above, and the ring nitrogen atom, when R is heteroaryl, is bonded via a carbon atom or optionally via a heteroatom, suitable for this purpose, of the heteroaryl.
  • Suitable six-membered heteroatomatic rings in the definition of the group G are:
  • the group G may be substituted by substituents selected from the group consisting of alkyl, alkyloxy, alkylthio, aryl, aryloxy, arylthio, halogen, CN, CHO, alkylcarbonyl, arylcarbonyl, carboxyl, alkyloxycarbonyl, aryloxycarbonyl, hydroxysulfonyl, alkyloxysulfonyl, aryloxysulfonyl, NO 2 and NO.
  • substituents mentioned comprise heteroatoms, they are bonded to the group G typically via carbon atoms of the group G. However, the bonding may also take place via suitable heteroatoms of the group G.
  • Preferred substituted groups G are: where R′′ is CN, CHO, alkylcarbonyl, arylcarbonyl, carboxyl, alkyloxycarbonyl, aryloxycarbonyl, hydroxysulfonyl, alkyloxysulfonyl, aryloxysulfonyl, NO 2 or NO, k′′ assumes values of 0 or 1, R and R′ are each independently alkyl or halogen, in particular fluorine, and k and k′ assume values of 0 or 1, with the proviso that, in group (Ga), the sum of k and k′ is 1 or 2 and, in group (Gb), the sum of k and k is 1 or 2 when k′′ assumes a value of 0, and the sum of k and k′′ is 0, 1 or 2 when k′′ assumes a value of 1.
  • the sum of k and k′ is preferably 2; in the case that k′′ assumes a value of 1, the sum of k and k′′ is preferably 0 or 2.
  • a value of 0 for k, k′ or k′′ means in this context that none of the R, R′ or R′′ substituents and thus a hydrogen atom is present at the corresponding position on the ring.
  • the substituents are preferably the same.
  • alkyl is in particular methyl, ethyl, n-propyl, isopropyl and tert-butyl.
  • Alkyl and aryl which are present in the corresponding radicals of the definition of R′′ are, respectively, in particular methyl, ethyl, n-propyl, isopropyl and tert-butyl, and phenyl, naphthyl, anthracenyl or phenanthrenyl, each of which may be substituted by substituents selected from the group consisting of methyl, F, Cl, phenoxy, methoxy, ethoxy, n-propoxy, isopropoxy and tert-butoxy, and preference is given to optionally substituted phenyl.
  • substituted groups include: n addition, the group G may also be fused to a further, optionally heteroatom-comprising ring, in which case the latter ring may itself be fused again.
  • Examples of such more highly fused groups G are: where X is O, S or NR where R is hydrogen, alkyl or aryl, and the two X′ are each independently a carbonyl group, CR 2 group, O, S or NR where R is hydrogen, alkyl or aryl.
  • Preferred fused groups G are: where X is defined as O, S or NR where R is hydrogen, alkyl or aryl, preferably hydrogen or alkyl.
  • Y 1 together with a group selected from chemical single bond, C(Y 4 ) 2 , C(O), O, S, S(O), SO 2 and NY 5 , may form a two-membered bridge B to that carbon atom or heteroatom of the bridge A which is in the a-position to the carbon atom which is bonded to the nitrogen atom of the carbene unit of the carbene ligand.
  • Y 4 and Y 5 are each independently alkyl, aryl or heteroaryl each as defined above, or hydrogen.
  • the two Y 4 in the bridge C(Y 4 ) 2 may be varied independently of one another, but they are preferably the same. More preferably, the two R 4 radicals are two hydrogen atoms or two methyl groups.
  • such substructures can be represented as: where the asterisk denotes the carbon atom or suitable heteroatom, in the a-position to the N-bonded vinylic carbon atom, of the bridge A, and B denotes the bridge composed of Y 1 and chemical single bond, C(Y 4 ) 2 , C(O), O, S, S(O), SO 2 or NY 5 .
  • the bridge B in each case consists of an ethylenediyl unit, in the formulae (Bc) and (Bd) in each case of a-CH 2 —X— unit in which X is defined as C(Y 4 ) 2 , C(O), O, S, S(O), SO 2 or NY 5 .
  • Y 1 and Y 2 additionally form an optionally fused aromatic ring, for example a benzene ring
  • X is in turn a chemical single bond, C(Y 4 ) 2 , C(O), O, S, S(O), SO 2 or NY 5 , and the symbol as before is a fusion of the benzene ring.
  • Preferred substructures are: where X is in particular O, S, a C(CH 3 ) 2 or SO 2 group.
  • Preferred inventive complexes of the formula I comprise one or more carbene ligands which are obtained by combination of substructures selected from the group of and selected from the group of
  • X ⁇ O, S, NR; R hydrogen or alkyl where the donor atom Do is preferably S or N—Y 3 , and Y 3 is preferably methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • Particularly preferred inventive complexes of the formula I comprise one or more carbene ligands which are obtained by combination of substructures selected from the group of and selected from the group of where the donor atom Do is preferably S or N—Y 3 and Y 3 is preferably methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • M is Ru(III), Rh(III), Ir(III), Pd(II) or Pt(II)
  • n is 3 for Ru(III), Rh(III) and Ir(III) and is 2 for Pd(II) and Pt(II)
  • Y 2 and Y 3 are each hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • Y 3 is preferably methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • inventive complexes of the formula I comprise one or more carbene ligands which are obtained by combination of substructures selected from the group of and selected from the group of where the donor atom Do is preferably S or N—Y 3 and Y 3 is preferably methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • M is Ru(III), Rh(III), Ir(III), Pd(II) or Pt(II)
  • n 3 for Ru(III), Rh(III) and Ir(III) and is 2 for Pd(II) and Pt(II)
  • Y 3 is hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • Y 3 is preferably methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • inventive complexes of the formula I comprise one or more carbene ligands which comprise substructures selected from the group of: where Do is defined as S or N—Y 3 and Y is defined as O, S, C(CH 3 ) 2 or SO 2, Y 2 is defined as hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl, and Y 3 is defined as methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • M is Ru(III), Rh(III), Ir(III), Pd(II) or Pt(II)
  • n assumes the value 3 for Ru(III), Rh(III) and Ir(III) and the value 2 for Pd(II) and Pt(II)
  • Y is defined as O, S, C(CH 3 ) 2 or SO 2
  • Do is defined as S or N—Y 3
  • Y 2 is defined as hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl
  • Y 3 is defined as methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • M is Ru(III), Rh(III) and in particular Ir(III), Pd(II) or Pt(II)
  • n assumes the value of 3 for Ru(II), Rh(III) and Ir(III), and the value of 2 for Pd(II) and Pt(II).
  • inventive complexes of the formula I comprise one or more carbene ligands which are obtained by combination of substructures selected from the group of where X is a CH 2 group or an oxygen atom and Y 1 is hydrogen, methyl, ethyl, isopropyl or tert-butyl,
  • M is Ru(III), Rh(III) and in particular Ir(III), Pd(II) or Pt(II)
  • n assumes the value of 3 for Ru(III), Rh(III) and Ir(III), and assumes the value of 2 for Pd(II) and Pt(II).
  • the complexes having trivalent metal centers ML′(L′′) 2 with two different carbene ligands L′ and L′′ are specified schematically L′ L′′ L 1 L 2 L 1 L 3 L 1 L 4 L 1 L 5 L 1 L 6 L 1 L 7 L 2 L 3 L 2 L 4 L 2 L 5 L 2 L 6 L 2 L 7 L 3 L 4 L 3 L 5 L 3 L 6 L 3 L 7 L 4 L 5 L 3 L 6 L 3 L 7 L 4 L 5 L 4 L 6 L 4 L 7 L 5 L 6 L 5 L 7 L 6 L 7 L 7 L 6 L 7 L 5 L 7 L 4 L 7 L 3 L 7 L 2 L 7 L 1 L 6 L 5 L 6 L 4 L 6 L 3 L 6 L 2 L 6 L 1 L 5 L 4 L 5 L 3 L 5 L 2 L 5 L 4 L 3 L 4 L 2 L 4 L 1 L 5 L 4 L 5 L 3 L 5 L 2 L 5 L 4 L 3 L 4 L 2 L 4 L 1 L 3 L 5 L 2 L 5 L 1 L 4 L 3 L 4 L 2 L 4 L 1 L
  • Y 2 is hydrogen, methyl, ethyl, n-propyl, isopropyl or tert-butyl
  • Y 3 is methyl, ethyl, n-propyl, isopropyl or tert-butyl.
  • L monoanionic, bidentate ligands
  • ligands L monoanionic, bidentate ligands
  • M is, for instance, Ru(III), Rh(III) or Ir(III), in particular Ir(III), and L′ and L′′ are each as defined above.
  • Possible ligands L are in particular acetylacetonate and derivatives thereof, picolinate, Schiff bases, amino acids, tetrakis(1-pyrazolyl)borates and the bidentate monoanionic ligands specified in WO 02/15645; in particular, acetylacetonate and picolinate are of interest.
  • the ligands L may be the same or different.
  • uncharged transition metal complexes are outstandingly suitable as emitter molecules in organic light-emitting diodes (OLEDs). Simple variations of the ligands or of the central metal make it possible to provide transition metal complexes which exhibit the electroluminescence in the red, green and in particular in the blue region of the electromagnetic spectrum. Uncharged transition metal complexes used in accordance with the invention are therefore suitable for use in industrially usable full color displays.
  • uncharged transition metal complexes are suitable as electron, exciton or hole blockers in OLEDs, depending upon the ligands used and the central metal used.
  • inventive transition metal-carbene complexes of the formula I may be prepared analogously to the processes known to those skilled in the art. Suitable preparation processes are detailed, for example, in the review articles W. A. Hermann et al., Advances in Organometallic Chemistry, Vol. 48, 1 to 69, W. A. Hermann et al., Angew. Chem. 1997, 109, 2256 to 2282 and G. Bertrand et al. Chem. Rev. 2000, 100, 39 to 91 and the literature cited therein.
  • the present application further provides a process for preparing the carbene complex of the formula I.
  • the inventive transition metal complexes of the formula I are prepared by deprotonating the ligand precursors corresponding to the particular carbene ligands and subsequently or simultaneously reacting with suitable metal complexes comprising the desired metal.
  • Suitable ligand precursors are known to those skilled in the art. They are preferably cationic precursors having negatively charged counterions.
  • the cationic precursors are reacted with a base, and the intermediates formed may be different depending upon the precursor.
  • the intermediates formed may be different depending upon the precursor.
  • what are formed are, for example, alkoxide derivatives, dimeric Wanzlick olefins or the free N-heterocycle carbenes.
  • Alkoxide derivatives and Wanzlick olefins are typically thermally stressed in the presence of a suitable metal precursor to eliminate the alcohol or to cleave the dimer, and the metal-carbene compound is formed in the presence of suitable metal complexes.
  • the reactions are typically carried out in suitable solvents which are known to those skilled in the art or can be determined by simple preliminary experiments, and it is possible in the case of two-stage variants to use the same solvent or different solvents for the two steps.
  • suitable solvents which are known to those skilled in the art or can be determined by simple preliminary experiments, and it is possible in the case of two-stage variants to use the same solvent or different solvents for the two steps.
  • Possible solvents available for selection are, for example, aromatic and aliphatic solvents or ethers, for example toluene, tetrahydrofuran, and additionally alcohols or chlorinated hydrocarbons such as methylene chloride, liquid ammonia, if appropriate in a mixture with tetrahydrofuran, and polar-aprotic solvents, for instance dimethylformamide, N-methylpyrrolidone or acetonitrile.
  • Alcohols and halogenated hydrocarbons are generally used only when no free carbene is formed in the reaction.
  • the base for the reaction with the ligand precursors may be present in the metal compounds which comprise the desired metal M of the complexes of the formula I.
  • Possible metal compounds are metal acetates, metal acetylacetonates, metal amides or metal alkoxylates.
  • the reaction may be effected with external bases such as KO t Bu, NaO t Bu, LiO t Bu, NaH, disilazides and phosphazene bases. It is also possible to carry out the reaction with the ligand precursors using the metal compounds comprising the base in combination with external bases.
  • the inventive transition metal-carbene complexes of the formula I are preferably obtained starting from the corresponding cationic precursors selected from the group consisting of azolium salts, in particular imidazolium salts, benzimidazolium salts; triazolium salts and azolidinium salts, in particular imidazolidinium salts, by reacting with an external base, preferably KO t Bu or disilazides, in particular, for example, potassium bis(trimethylsilyl)amide, and subsequent or in situ reaction of the resulting intermediate with a complex of the desired metal.
  • azolium salts in particular imidazolium salts, benzimidazolium salts
  • triazolium salts and azolidinium salts in particular imidazolidinium salts
  • Suitable complexes of the desired metal are known to those skilled in the art.
  • the desired metal in the metal complex used and the corresponding metal of the transition metal-carbene complex I prepared therefrom do not have to have the same oxidation state.
  • iridium(III) complexes of the general formula I which are particularly preferred according to the present application, it is possible, for example, to use the following iridium(III) complexes: [( ⁇ -Cl)Ir( ⁇ 4 -1,5-cod)] 2 , [( ⁇ -Cl)Ir( ⁇ 2 -1,5-coe) 2 ] 2 , Ir(acac) 3 , IrCl 3 .n H 2 O, (tht) 3 IrCl 3 , where cod is cyclooctadiene, coe is cyclooctene, acac is acetylacetonate and tht is tetrahydrothiophene.
  • Alkoxide derivatives or Wanzlick olefins are typically added at room temperature to the appropriate metal precursors and subsequently thermally stressed, in the course of which the corresponding alcohol is eliminated in the case of the alkoxide derivatives, or the dimeric Wanzlick olefins are cleaved, and the metal-carbene compound is formed.
  • these reactions take place at temperatures of from 20 to 160° C.
  • the intermediates used are to be free carbenes (e.g. imidazolin-2-ylidenes)
  • they are generally added to the metal precursor with cooling, subsequently warmed to room temperature (20 to 25° C.) and/or if appropriate to even higher temperature.
  • the reaction is carried out within a temperature range of from ⁇ 78 to +160° C.
  • the ratio of metal complex used to ligand precursor used is dependent upon the desired complex which bears at least two carbene ligands.
  • the metal atom is Ir(III), which is particularly preferred, and the desired transition metal complex comprises three carbene ligands, which is likewise particularly preferred
  • the molar amount of ligand precursors has to be about three times as large as the molar amount of metal in the metal complex, and a small excess of the ligand precursor may be used.
  • the molar ratio of metal in the metal complex to the molar amount of ligand precursors is generally from 1:3 to 1:6.
  • the molar ratio of base used to ligand precursor used is typically from 3:1 to 1:1, preferably from 2:1 to 1:1.
  • strong bases such as LiO t Bu, NaO t Bu, KO t Bu or potassium bis(trimethylsilyl)amide (KHMDS) are used, a molar ratio of base to ligand precursor of 1:1 is generally sufficient.
  • X ⁇ is an anionic group, preferably a halide, pseudohalide or another monoanionic group, for example Cl ⁇ , Br ⁇ , I ⁇ , BF 4 ⁇ , PF 6 ⁇ , CN ⁇ , SCN ⁇ , more preferably BF 4 ⁇ , PF 6 ⁇ .
  • the transition metal-carbene complexes used in accordance with the invention are outstandingly suitable as emitter substances, since they have an emission (electroluminescence) in the visible region of the electromagnetic spectrum. With the aid of the transition metal-carbene complexes used in accordance with the invention as emitter substances, it is possible to provide compounds which have electroluminescence in the red, green and in the blue region of the electromagnetic spectrum. It is thus possible with the aid of the transition metal-carbene complexes used in accordance with the invention as emitter substances to provide industrially usable full color displays.
  • the aforementioned uncharged transition metal complexes are suitable as electron, exciton or hole blockers in OLEDs, depending on the ligands used and the central metal used.
  • Organic light-emitting diodes are in principle composed of several layers:
  • the OLED does not have all of the layers mentioned; for example an OLED having the layers (1) (anode), (3) (light-emitting layer) and (5) (cathode) is likewise suitable, in which case the functions of the layers (2) (hole-transporting layer) and (4) (electron-transporting layer) are assumed by the adjacent layers. OLEDs which have the layers (1), (2), (3) and (5), or the layers (1), (3), (4) and (5), are likewise suitable.
  • the transition metal-carbene complexes according to the present application may be used in various layers of an OLED.
  • the present invention therefore further provides an OLED comprising at least one transition metal-carbene complex according to the present application.
  • the transition metal-carbene complexes are used preferably as emitter molecules in the light-emitting layer.
  • the present invention therefore further provides a light-emitting layer comprising at least one transition metal-carbene complex as an emitter molecule.
  • Preferred transition metal-carbene complexes, in particular transition metal-carbene complexes having N-heterocyclic carbene ligands, have already been specified above.
  • inventive transition metal-carbene complexes may be present in bulk, without further additives, in the light-emitting layer or another layer of the OLED, preferably in the light-emitting layer.
  • further compounds are present in the layers comprising at least one transition metal-carbene complex according to the present application, preferably in the light-emitting layer.
  • a fluorescent dye may be present in the light-emitting layer in order to alter the emission color of the transition metal-carbene complex used as an emitter molecule.
  • a diluent material may be used.
  • This diluent material may be a polymer, for example poly(N-vinylcarbazole) or polysilane. However, the diluent material may likewise be a small molecule, for example 4,4′-N,N′-dicarbazolebiphenyl (CDP ⁇ CBP) or tertiary aromatic amines.
  • CDP ⁇ CBP 4,4′-N,N′-dicarbazolebiphenyl
  • the proportion of the transition metal-carbene complexes used in accordance with the invention in the light-emitting layer is generally less than 60% by weight, preferably less than 50% by weight, more preferably from 5 to 40% by weight.
  • the individual aforementioned layers of the OLED may be composed of 2 or more layers.
  • the hole-transporting layer may be composed of one layer into which holes are injected from the electrode and one layer which transports the holes from the hole-injecting layer away into the light-emitting layer.
  • the electron-transporting layer may likewise consist of a plurality of layers, for example one layer in which electrons are injected by the electrode and one layer which receives electrons from the electron-injecting layer and transports them into the light-emitting layer.
  • These specified layers are each selected according to factors such as energy level, thermal resistance and charge carrier mobility, and also energy differential of the layers mentioned with the organic layers or the metal electrodes.
  • Those skilled in the art are capable of selecting the structure of the OLEDs in such a way that it is adapted optimally to the transition metal-carbene complexes used as emitter substances in accordance with the invention.
  • the HOMO (highest occupied molecular orbital) of the hole-transporting layer should be aligned to the work function of the anode, and the LUMO (lowest unoccupied molecular orbital) of the electron-transporting layer aligned to the work function of the cathode.
  • the present application further provides an OLED comprising at least one inventive light-emitting layer.
  • the further layers in the OLED may be composed of any material which is typically used in such layers and is known to those skilled in the art.
  • the anode (1) is an electrode which provides positive charge carriers. It may be composed, for example, of materials which comprise a metal, a mixture of different metals, a metal alloy, a metal oxide or a mixture of different metal oxides. Alternatively, the anode may be a conductive polymer. Suitable metals comprise the metals of groups 11, 4, 5 and 6 of the Periodic Table of the Elements, and also the transition metals of groups 8 to 10. When the anode is to be transparent, mixed metal oxides of groups 12, 13 and 14 of the Periodic Table of the Elements are generally used, for example indium tin oxide (ITO). It is likewise possible that the anode (1) comprises an organic material, for example polyaniline, as described, for example, in Nature, Vol. 357, pages 477 to 479 (Jun. 11, 1992). At least either the anode or the cathode should be at least partly transparent in order to be able to omit the light formed.
  • ITO indium tin oxide
  • Suitable hole-transporting materials for the layer (2) of the inventive OLED are disclosed, for example, in Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition, Vol. 18, pages 837 to 860, 1996. Either hole-transporting molecules or polymers may be used as the hole-transporting material.
  • Customarily used hole-transporting molecules are selected from the group consisting of 4,4′-bis[N-(1-naphthyl)-N-phenylamino]biphenyl ( ⁇ -NPD), N,N′-diphenyl-N,N′-bis(3-methylphenyl)-[1,1′-biphenyl]-4,4′-diamine (TPD), 1,1-bis[(di-4-tolylamino)phenyl]cyclohexane (TAPC), N,N′-bis(4-methylphenyl)-N,N′-bis(4-ethylphenyl)-[1,1′-(3,3′-dimethyl)biphenyl]-4,4′-diamine (ETPD), tetrakis-(3-methylphenyl)-N,N,N′,N′-2,5-phenylenediamine (PDA), a-phenyl-4-N,N-diphenyla
  • Customarily used hole-transporting polymers are selected from the group consisting of polyvinylcarbazoles, (phenylmethyl)polysilanes, PEDoT (poly(3,4-ethylenedioxythiophene)), preferably PEDoT doped with PSS (polystyrene sulfonate), and polyanilines. It is likewise possible to obtain hole-transporting polymers by doping hole-transporting molecules into polymers such as polystyrene and polycarbonate. Suitable hole-transporting molecules are the molecules already mentioned above.
  • oxinoid compounds such as tris(8-quinolinolato)-aluminum (Alq 3 )
  • the layer (4) may serve both to ease the electron transport and as a buffer layer or as a barrier layer in order to prevent quenching of the exciton at the interfaces of the layers of the OLED.
  • the layer (4) preferably improves the mobility of the electrons and reduces quenching of the exciton.
  • hole-transporting materials and electron-transporting materials some can fulfill a plurality of functions.
  • some of the electron-conducting materials are simultaneously hole-blocking materials when they have a low-lying HOMO.
  • the charge transport layers may also be electronically doped in order to improve the transport properties of the materials used, in order firstly to make the layer thicknesses more generous (avoidance of pinholes/short circuits) and secondly to minimize the operating voltage of the device.
  • the hole-transporting materials may be doped with electron acceptors; for example, phthalocyanines or arylamines such as TPD or TDTA may be doped with tetrafluorotetracyanoquinodimethane (F4-TCNQ).
  • the electron-transporting materials may, for example, be doped with alkali metals, for example Alq 3 with lithium. Electronic doping is known to those skilled in the art and is disclosed, for example, in W. Gao, A. Kahn, J.
  • the cathode (5) is an electrode which serves to introduce electrons or negative charge carriers.
  • Suitable materials for the cathode are selected from the group consisting of alkali metals of group 1, for example Li, Cs, alkaline earth metals of group 2, for example calcium, barium or magnesium, metals of group 12 of the Periodic Table of the Elements, comprising the lanthanides and actinides, for example samarium.
  • metals such as aluminum or indium, and combinations of all of the metals mentioned, may also be used.
  • lithium-comprising organometallic compounds or LiF may be applied between the organic layer and the cathode in order to reduce the operating voltage.
  • the OLED of the present invention may additionally comprise further layers which are known to those skilled in the art.
  • a layer which eases the transport of the positive charge and/or matches the band gaps of the layers to one another may be applied between the layer (2) and the light-emitting layer (3).
  • this further layer may serve as a protective layer.
  • additional layers may be present between the light-emitting layer (3) and the layer (4) in order to ease the transport of the negative charge and/or to match the band gaps between the layers to one another.
  • this layer may serve as a protective layer.
  • the inventive OLED in addition to the layers (1) to (5), comprises at least one of the further layers mentioned below:
  • the OLED does not have all of the layers (1) to (5) mentioned; for example, an OLED having the layers (1) (anode), (3) (light-emitting layer) and (5) (cathode) is likewise suitable, in which case the functions of the layers (2) (hole-transporting layer) and (4) (electron-transporting layer) are assumed by the adjacent layers. OLEDs which have the layers (1), (2), (3) and (5) or the layers (1), (3), (4) and (5) are likewise suitable.
  • Suitable materials for the individual layers are known to those skilled in the art and disclosed, for example, in WO 00/70655.
  • each of the specified layers of the inventive OLED may be composed of two or more layers.
  • the selection of the materials for each of the layers mentioned is preferably determined by obtaining an OLED having a high efficiency and lifespan.
  • the inventive OLED can be produced by methods known to those skilled in the art.
  • the OLED is produced by successive vapor deposition of the individual layers onto a suitable substrate.
  • Suitable substrates are, for example, glass or polymer films.
  • customary techniques may be used, such as thermal evaporation, chemical vapor deposition and others.
  • the organic layers may be coated from solutions or dispersions in suitable solvents, in which case coating techniques known to those skilled in the art are employed.
  • Compositions which, in addition to the at least one inventive transition metal-carbene complex, have a polymeric material in one of the layers of the OLED, preferably in the light-emitting layer, are generally applied as a layer by means of solution-mediated processes.
  • the different layers have the following thicknesses: anode (1) from 500 to 5000 ⁇ , preferably from 1000 to 2000 ⁇ ; hole-transporting layer (2) from 50 to 1000 ⁇ , preferably from 200 to 800 ⁇ ; light-emitting layer (3) from 10 to 1000 ⁇ , preferably from 100 to 800 ⁇ ; electron-transporting layer (4) from 50 to 1000 ⁇ , preferably from 200 to 800 ⁇ ; cathode (5) from 200 to 10 000 ⁇ , preferably from 300 to 5000 ⁇ .
  • the position of the recombination zone of holes and electrons in the inventive OLED and thus the emission spectrum of the OLED may be influenced by the relative thickness of each layer.
  • the thickness of the electron transport layer should preferably be selected such that the electron/hole recombination zone is within the light-emitting layer.
  • the ratio of the layer thicknesses of the individual layers in the OLED is dependent upon the materials used. The layer thicknesses of any additional layers used are known to those skilled in the art.
  • transition metal-carbene complexes used in accordance with the invention in at least one layer of the OLED, preferably as emitter molecules in the light-emitting layer of the inventive OLEDs, allows OLEDs having a high efficiency to be obtained.
  • the efficiency of the inventive OLEDs may additionally be improved by optimizing the other layers.
  • highly efficient cathodes such as Ca or Ba, if appropriate in combination with an intermediate layer of LiF, may be used.
  • Shaped substrates and novel hole-transporting materials which bring about a reduction in the operating voltage or an increase in the quantum efficiency are likewise usable in the inventive OLEDs.
  • additional layers may be present in the OLEDs in order to adjust the energy level of the different layers and to ease electroluminescence.
  • the inventive OLEDs may be used in all devices in which electroluminescence is useful. Suitable devices are preferably selected from stationary and mobile visual display units (VDUs). Stationary VDUs are, for example, VDUs of computers, televisions, VDUs in printers, kitchen appliances and advertising panels, illuminations and information panels. Mobile VDUs are, for example, VDUs in mobile telephones, laptops, digital cameras, vehicles and destination displays on buses and trains.
  • VDUs stationary and mobile visual display units
  • transition metal-carbene complexes used in accordance with the invention may be used in OLEDs having inverse structure.
  • the structure of inverse OLEDs and the materials customarily used therein are known to those skilled in the art.
  • inventive transition metal complexes may, in addition to the use in OLEDs, be used as colorants which emit in the visible region of the electromagnetic spectrum on irradiation by light (photoluminescence). Such colorants are used preferably as colorants in polymeric materials.
  • the present application therefore further provides for the use of the above-described inventive transition metal-carbene complexes or those used in accordance with the invention for the bulk coloration of polymeric materials.
  • Suitable polymeric materials are polyvinyl chloride, cellulose acetate, polycarbonates, polyamides, polyurethanes, polyimides, polybenzimidazoles, melamine resins, silicones, polyesters, polyethers, polystyrene, polymethyl methacrylate, polyethylene, polypropylene, polyvinyl acetate, polyacrylonitrile, polybutadiene, polychlorobutadiene, polyisoprene and the copolymers of the monomers listed.
  • inventive transition metal complexes or those used in accordance with the invention may be used in the following applications:
  • a 500 l three-neck flask is initially charged with 10 g (32 mmol) of imidazolium iodide in 150 ml of toluene and 64.3 ml of potassium bis(trimethylsilyl)amide (0.5 M in toluene, 32 mmol) are added at room temperature within 30 minutes. The mixture is left to stir at room temperature for 30 minutes. 2.16 g (3.2 mmol) of [( ⁇ -Cl)( ⁇ 4 -1,5-cod)Ir] 2 are then dissolved in 200 ml of toluene and admixed dropwise with the salt mixture at room temperature. The reaction mixture is stirred at room temperature for one hour, at 70° C. for 2 hours and then under reflux overnight. The mixture is subsequently concentrated to dryness and the residue is extracted with methylene chloride. After again concentrating to dryness, the brown residue is subjected to purification by column chromatography. 1.15 g of a yellow powder (24% of theory) are obtained.
  • Elemental analysis (calculated value for empirical formula IrC 33 H 24 N 9 ): calculated (% by wt.) found (% by wt.) Carbon 53.7 54.0 Nitrogen 17.1 16.2 Hydrogen 3.3 3.7
  • Thermogravimetry/differential thermoanalysis (heating rate: 5K/min): Loss of solvent at from approx. 100° C. to 160° C. Start of decomposition from approx. 370° C.
  • the ITO substrate used as an anode is cleaned first with commercial detergents for LCD production (Deconex® 20NS and 25ORGAN-ACID® neutralizing agent) and then in an ultrasound bath in an acetone/isopropanol mixture. To remove possible organic residues, the substrate is exposed to a continuous ozone flow in an ozone oven for a further 25 minutes. This treatment also improves the hole injection of the ITO.
  • the organic materials specified below are applied to the cleaned substrate by vapor deposition at a rate of approx. 2 nm/min at about 10-7 mbar.
  • 1-TNATA 4,4′,4′′-tris(N-(naphth-1-yl)-N-phenylamino)triphenylamine
  • 1-TNATA 4,4′,4′′-tris(N-(naphth-1-yl)-N-phenylamino)triphenylamine
  • a mixture of 34% by weight of the compound 1 c) from example 1 c) and 66% by weight of the compound C2 (1,3-phenylene-10,10′-bis(phenothiazine)5,5′-dioxide) is applied by vapor deposition in a thickness of 20 nm, the former compound serving as the emitter, the latter as the matrix material.
  • a hole blocker and electron conductor layer of 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (BCP) in a thickness of 47.5 nm, a 0.75 nm-thick lithium fluoride layer and finally a 110 nm-thick Al electrode are applied by vapor deposition.
  • the electroluminescence spectra are recorded at various currents and voltages.
  • the current-voltage characteristic is measured in combination with the emitted light output.
  • the light output can be converted to photometric parameters by calibration with a photometer.
  • the compound C2 was prepared as follows:
  • the ITO substrate is pretreated as described under a).
  • the organic materials specified below are applied to the cleaned substrate by vapor deposition at a rate of approx. 2 nm/min at about 10 ⁇ 7 mbar.
  • 1-TNATA(4,4′,4′′-tris(N-(naphth-1-yl)-N-phenylamino)triphenylamine) is applied first to the substrate in a layer thickness of 15 mm. This is followed by the application by vapor deposition of a 9 mm-thick exciton blocker layer of the compound C1.
  • a mixture of 55% by weight of the compound 1 c) and 45% by weight of 1,3-bis(N-carbazolyl)benzene is applied by vapor deposition in a thickness of 16 nm, the former compound serving as the emitter, the latter as the matrix material.
  • a hole blocker and electron conductor layer of BCP in a thickness of 45 nm, a 0.75 nm-thick lithium fluoride layer and finally a 110 nm-thick Al electrode are applied by vapor deposition.
  • the electroluminescence spectra are recorded at various currents and voltages.
  • the current-voltage characteristic is measured in combination with the emitted light output.
  • the light output can be converted to photometric parameters by calibration with a photometer.
  • the ITO substrate is pretreated as described under a).
  • PEDT:PSS poly(3,4-ethylenedioxythiophene)poly(styrenesulfonate)
  • Baytron® P VP Al 4083 is spin-coated from aqueous solution onto the substrate in a thickness of 46 nm and the emitter layer is applied in a thickness of approx. 48 nm from PMMA dissolved in chlorobenzene (16.5 mg of PMMA for 1 ml of chlorobenzene) and the emitter substance 1c).
  • the concentration of the emitter corresponds to a 30% by weight doping of PMMA.
  • a hole blocker and electron conductor layer of BCP in a thickness of 52.5 nm, a 0.75 nm-thick lithium fluoride layer and finally a 110 nm-thick Al electrode are applied by vapor deposition.
  • electroluminescence spectra are recorded at various currents and voltages.
  • the current-voltage characteristic is measured in combination with the emitted light output.
  • the light output may be converted to photometric parameters by calibration with a photometer.

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  • Engineering & Computer Science (AREA)
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  • Crystallography & Structural Chemistry (AREA)
  • Inorganic Chemistry (AREA)
  • Electroluminescent Light Sources (AREA)
  • Plural Heterocyclic Compounds (AREA)
  • Nitrogen And Oxygen Or Sulfur-Condensed Heterocyclic Ring Systems (AREA)
  • Organic Low-Molecular-Weight Compounds And Preparation Thereof (AREA)
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DE102004057072.8 2004-11-25
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ATE435867T1 (de) 2009-07-15
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WO2006056418A8 (de) 2007-03-01
US20140309428A1 (en) 2014-10-16
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US11980086B2 (en) 2024-05-07
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JP2008521946A (ja) 2008-06-26
US20200136064A1 (en) 2020-04-30
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US20240074302A1 (en) 2024-02-29
KR20070090953A (ko) 2007-09-06
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CN101065389A (zh) 2007-10-31
CN101065389B (zh) 2012-05-09

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