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WO2009087064A1 - Matières dendritiques hôte-invité ioniques électroluminescentes - Google Patents

Matières dendritiques hôte-invité ioniques électroluminescentes Download PDF

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Publication number
WO2009087064A1
WO2009087064A1 PCT/EP2008/068224 EP2008068224W WO2009087064A1 WO 2009087064 A1 WO2009087064 A1 WO 2009087064A1 EP 2008068224 W EP2008068224 W EP 2008068224W WO 2009087064 A1 WO2009087064 A1 WO 2009087064A1
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substituted
unsubstituted
alkyl
group
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Gerard Van Koten
Aidan Mcdonald
Roger PRÉTÔT
Roman Kolly
Oliver Dosenbach
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BASF Schweiz AG
BASF SE
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Ciba Holding AG
BASF SE
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    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic Table compounds of the platinum group
    • C07F15/0033—Iridium compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/20—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the material in which the electroluminescent material is embedded
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/10—Non-macromolecular compounds
    • C09K2211/1018—Heterocyclic compounds
    • C09K2211/1025—Heterocyclic compounds characterised by ligands
    • C09K2211/1029—Heterocyclic compounds characterised by ligands containing one nitrogen atom as the heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/18—Metal complexes
    • C09K2211/185—Metal complexes of the platinum group, i.e. Os, Ir, Pt, Ru, Rh or Pd

Definitions

  • the invention relates to novel electroluminescent ionic host-guest compounds, especially anionic organometallic phosphorescent emitters embedded in a cationic dendritic species, electronic devices comprising the electroluminescent ionic compounds and their use in electronic devices, especially organic light emitting diodes (OLEDs).
  • OLEDs organic light emitting diodes
  • Organic electronic devices that emit light, such as light emitting diodes that make up displays, are present in many different kinds of electronic equipment.
  • an organic active layer is sandwiched between two electrical contact layers. At least one of the electrical contact layers is light-transmitting so that light can pass through the electrical contact layer.
  • the organic active layer emits light through the light-transmitting electrical contact layer upon application of a voltage across the contact layers.
  • Organic electrophosphorescent compounds known for use as an active component in a light emitting diode include various metal complexes comprising, for example, homoleptic
  • electroluminescent compounds with excellent light emitting characteristics and good processability which may provide good control at a molecular level and for guest-host systems with a high level of the guest molecule in order to provide devices having improved efficiency.
  • the properties of dendrimers make them ideal for solution processing and allow incorporation of metal complex chromophores through ionic interaction at definite sites which are predetermined by the cationic charge of the core resulting in separating the adjacent metal complexes and reduced triplet-triplet quenching.
  • the number of guest molecules can be varied by varying the number of charges of the core. Controlled by the generation of the dendrimer the active metal complex may be completely embedded in the shell which leads to an increased lifetime of the light emitting device.
  • E 1 is unsubstituted or substituted Ci-Ci 8 alkylene or unsubstituted or substituted
  • R 1 and R 2 independently are H, unsubstituted or substituted Ci-Ci 8 alkyl, or R 1 and R 2 form an organic bridging group completing, together with the nitrogen atom, they are bonding to, a heterocyclic ring of 5 to 7 ring atoms in total;
  • L 1 M is a fragment of a metal complex
  • M is a metal with an atomic weight greater than 40
  • L 1 independently is a color emission triggering moiety, comprising mono- or bidentate ligands
  • L 2 is a mono- or bidentate ligand, substituted by Y-Z " , wherein
  • Y is a single bond, unsubstituted or substituted Ci-Ci 8 alkylene or unsubstituted or substituted
  • Ci-Ci 8 alkyleneoxy optionally interrupted by O or S;
  • Z “ is an anionic group of sulfate (OSO 3 " ), sulfonate (SO 3 “ ), carboxylate (CO 2 " ), phosphate
  • X " is an equivalent of a suitable anion.
  • the ionic compound is of formula (II)
  • A is a n-valent radical selected from H, Si, C, P, hydrocarbon radicals of 1 to 150 carbon atoms, and hydrocarbon radicals of 2 to 150 carbon atoms, wherein 1 or more CH 2 have been replaced by O, S, NR 3 , or N + R 3 R 3 , one or more CH have been replaced by P or N, or - A -
  • each Ar 1 independently is unsubstituted or substituted C 6 -Ci 4 arylene
  • each D independently is a dendritic molecular structure, comprising at least one branching group and optionally at least one linking group, the branching group being selected from unsubstituted or substituted C 6 -Ci 4 arylene and unsubstituted or substituted CrCi 8 alkylene, and the linking group being selected from unsubstituted or substituted C ⁇ -C-uarylene, unsubstituted or substituted CrCi 8 alkylene, unsubstituted or substituted Ci-Ci 8 alkyleneoxy and oxygen, said branching group being bonded to three or more groups, and said linking group being bonded to two groups, said dendritic molecular structure terminating at its distal points in unsubstituted or substituted C 6 -Ci
  • R 4 , R 5 , R 6 independently are H, unsubstituted or substituted Ci-Ci 8 alkyl, unsubstituted or
  • R 4 ', R 5 ', R 6 ' independently are unsubstituted or substituted Ci-Ci 8 alkyl, unsubstituted or substituted C 6 -Ci 4 aryl, OH, unsubstituted or substituted Ci-Ci 8 alkoxy, or a moiety of formula
  • A represents a linking group E 2 , wherein E 2 is a direct bond, oxygen, unsubstituted or substituted Ci-Ci 8 alkylene, or a group -[Ar 2 Jr, wherein Ar 2 is unsubstituted or substituted C 6 -Ci 4 arylene, and r is an integer of from 1 to 10; or A is R 4 R 5 Si-E 2 -SiR 4 R 5' .
  • dendrimer represents highly ordered, regularly branched, globular macromolecules prepared by a stepwise iterative approach. Their structure is divided in a core and one or more dendrons (also called dendrites or dendritic structure) attached to the core.
  • dendrons also called dendrites or dendritic structure
  • dendrimer does not encompass a hyperbranched polymer which has been synthesized through polymerization and which, as a result, has an irregularly arranged branching structure.
  • the cationic dendrimer constituting a part of the present invention of formula (II) is known or is of a structure analogous to known compounds (Kleij, A.W. et al, Organometallics 1999, 18, 268-276 and Kleij, A.W. et al, Chem. Eur. J. 2001 , 7, 181-192).
  • the dendrimer of the present invention has a branching structure in which repeating units each having a branching group are repeatedly linked through the "convergent method". This method is described in detail in Grayson, S. M., Frechet, J.M.J., Chem. Rev. 2001 , 101 , 3819-3867 or Hawker, CJ. , Frechet, J.M.J., J. Am. Chem. Soc. 1990, 112, 7638-7647. Therein, the dendrons are at first grown to the desired generation, and the resulting dendritic wedges are finally bonded to one or more focal points of a core.
  • the core of a dendrimer serves as a center moiety, which is linked to one or more dendrons.
  • the core is characterized in that it comprises at least one cationic moiety of the formula
  • each nitrogen atom of the quaternary ammonium groups is bonded to a carbon atom of a dendron D, i.e. the number of quaternary ammonium groups defines the number of the charge of the core and thus the number of bonded dendrons.
  • One or more cationic moieties of formula (IN') are bonded to a group A, which represents a n-valent radical, preferably selected from H, Si, C, and an hydrocarbon radical of 1 to 60 carbon atoms and hydrocarbon radicals of 2 to 60 carbon atoms, wherein 1 or more CH 2 have been replaced by O, S, NR 3 or N + R 3 R 3 , one or more CH have been replaced by P or N, or one or more C have been replaced by Si.
  • a group A which represents a n-valent radical, preferably selected from H, Si, C, and an hydrocarbon radical of 1 to 60 carbon atoms and hydrocarbon radicals of 2 to 60 carbon atoms, wherein 1 or more CH 2 have been replaced by O, S, NR 3 or N + R 3 R 3 , one or more CH have been replaced by P or N, or one or more C have been replaced by Si.
  • Hydrocarbon radicals of 1 to 60 carbon atoms are, for example, groups CR 4 R 5 R 6 , wherein R 4 , R 5 , R 6 independently are H, unsubstituted or substituted CrCi 8 alkyl, unsubstituted or substituted C 6 -Ci 4 aryl.
  • Hydrocarbon radicals of 2 to 60 carbon atoms, wherein one or more C have been replaced by Si are, for example, groups SiR 4 R 5 R 6 , wherein R 4 ,R 5 and R 6 independently are unsubstituted or substituted CrCi 8 alkyl, unsubstituted or substituted C 6 -Ci 4 aryl, OH, or unsubstituted or substituted Ci-Ci 8 alkoxy.
  • Hydrocarbon radicals of 2 to 60 carbon atoms wherein one or more CH 2 have been replaced by O, S, NR 3 or N + R 3 R 3 , one or more CH have been replaced by P or N, or one or more C have been replaced by Si are, for example, groups CR 4 R 5 R 6 , wherein R 4 , R 5 , R 6 independently are H, unsubstituted or substituted CrCi 8 alkyl, unsubstituted or substituted
  • Hydrocarbon radicals of 2 to 60 carbon atoms wherein one or more CH 2 have been replaced by O, S, NR 3 or N + R 3 R 3 , one or more CH have been replaced by P or N, or one or more C have been replaced by Si are, for example, groups SiR 4 R 5 R 6 , wherein R 4 , R 5 and R 6 independently are unsubstituted or substituted CrCi 8 alkyl, unsubstituted or substituted C 6 -Ci 4 aryl, OH, or unsubstituted or substituted Ci-Ci 8 alkoxy and optionally a moiety of
  • Hydrocarbon radicals of 2 to 60 carbon atoms wherein one or more CH 2 have been replaced by O, S or NR 3 or one or more CH have been replaced by P or N, are, for example, heterocyclic rings, preferably aromatic or aliphatic heterocyclic rings of 5 or 6 atoms in total, containing 1 to 3 nitrogen atoms or 1 sulfur atom, such as 1 ,2,3-triazole, 1 ,2,4-triazole, triazine, pyridine, piperazine, or thiophene, all of which may be substituted or fused to another carbocyclic or heterocyclic ring.
  • heterocyclic rings preferably aromatic or aliphatic heterocyclic rings of 5 or 6 atoms in total, containing 1 to 3 nitrogen atoms or 1 sulfur atom, such as 1 ,2,3-triazole, 1 ,2,4-triazole, triazine, pyridine, piperazine, or thiophene, all of which may be substituted or fused to another carbo
  • the group A may be a group of formula (I') R R , which results in a polycationic
  • R-' V R 1 R 2 dendrimer of the following structure with (p+1 ) quaternary nitrogen atoms.
  • A may be a linking group E 2 , wherein E 2 is a direct bond, oxygen, unsubstituted or substituted CrCi 8 alkylene, or a group Of -[Ar 2 Jr, wherein Ar 2 is unsubstituted or substituted C 6 -Ci 4 arylene and r is 1 to 10, or E 2 is R 4 R 5 Si-E 2 -SiR 4 R 5' .
  • Ar 2 may also be a heterocyclic ring, preferably an aromatic or aliphatic heterocyclic ring of 5 or 6 atoms in total, containing 1 to 3 nitrogen atoms or 1 sulfur atom, such as 1 ,2,3-triazole, 1 ,2,4-triazole, triazine, pyridine, piperazine, or thiophene, all of which may be substituted or fused to another carbocyclic or heterocyclic ring.
  • a heterocyclic ring preferably an aromatic or aliphatic heterocyclic ring of 5 or 6 atoms in total, containing 1 to 3 nitrogen atoms or 1 sulfur atom, such as 1 ,2,3-triazole, 1 ,2,4-triazole, triazine, pyridine, piperazine, or thiophene, all of which may be substituted or fused to another carbocyclic or heterocyclic ring.
  • the cationic dendrimer i.e. the cationic part of formula (II), has the following structure of formula (IV)
  • R 1 , R 2 independently are Ci-C 4 alkyl, preferably methyl
  • E 1 is Ci-C 4 alkylene.
  • ionic compounds wherein the cationic dendrimer, i.e. the cationic part of formula (II), has the following structure of formulae (V) or (Vl)
  • Suitable cationic dendrimers include
  • Dendrons or dendritic structures are branched structures comprising branching groups and optionally linking groups.
  • the generation of a dendron is defined by the number of sets of branching points.
  • Dendrons of higher generation can be composed of the same structural units (branching and linking groups) but have an additional level of branching, i.e. an additional repetition of these branching and linking groups. Alternatively higher generations can have an additional level of branching but different branching and linking groups at the higher generation.
  • Branching groups have three or more attachments.
  • the branching group may be unsubstituted or substituted C 6 -Ci 4 arylene and/or unsubstituted or substituted d- Ci 8 alkylene.
  • Linking groups if present, have two attachments and may be unsubstituted or substituted C 6 -Ci 4 arylene and/or unsubstituted or substituted Ci-Ci 8 alkylene and/or unsubstituted or substituted Ci-Ci 8 alkyleneoxy and/or an oxygen atom.
  • the arylene groups within the dendrons may be typically benzene, naphthalene, anthracene, phenanthrene or biphenylene (in which case an aryl group is present in the link between adjacent branching groups), fluorene and where appropriate substituted variations.
  • Typical substituents which may be present at any position, include CrCi 8 alkyl, Ci-Ci 8 alkoxy, halogen and CF 3 .
  • the arylene groups at the branching points are preferably benzene rings, preferably coupled at ring positions 1 , 3 and 5.
  • the dendrons may be of the same or different generation as well as of the same or different type. Preferred are dendrons of the same generation and type.
  • dendritic structures D include the following groups, wherein (Vl 1-1 ) to (VII-3) are preferred and (Vl 1-1 ) is most preferred:
  • the number of generations of the dendrons is preferably 1 to 6 and more preferably 1 , 2 or 3.
  • ionic compounds wherein the dendritic molecular structure D is of the 1 st , 2 nd or 3 rd generation.
  • distal denotes the part or parts of the molecule furthest from the core when following the bond sequence out from the core.
  • the distal groups are unsubstituted or substituted C 6 -Ci 4 aryl and/or unsubstituted or substituted Ci-Ci 8 alkyl and/or OH, and/or unsubstituted or substituted Ci-Ci 8 alkoxy.
  • the anionic part of the ionic dendritic compound of the present invention i.e. the anionic metal complex L 1 M(L 2 - Y-Z " ), is characterized in that one ligand attached to the metal cation has an anionic substituent Z " , which is located close to the ammonium group of the dendrimer by electrostatic forces. Also, the compound of formula (II) is electroneutral.
  • the group L 1 M represents a fragment of a metal complex comprising one or more ligands L 1 attached to the metal cation M.
  • All ligands L 1 and the group (L 2 - Y-Z " ) attached to the metal cation must be such that the coordination requirements of the metal cation are fullfilled.
  • Preferred ligands L 1 and L 2 as well as metal cations M are described below.
  • ligand is intended to mean a molecule, ion, or atom that is attached to the coordination sphere of a metallic ion.
  • complex when used as a noun, is intended to mean a compound having at least one metallic ion and at least one ligand.
  • group is intended to mean a part of a compound, such a substituent in an organic compound or a ligand in a complex.
  • adjacent to when used to refer to layers in a device, does not necessarily mean that one layer is immediately next to another layer.
  • photoactive refers to any material that exhibits electroluminescence and/or photosensitivity.
  • the metal M of the fragment L 1 M of the present invention is generally a metal with an atomic weight of greater than 40, preferably the metal M is selected from Tl, Pb, Bi, In, Sn, Sb, Te, especially Mo, Cr, Mn, Ta, V, Cu, Fe, Ru, Ni, Co, Ir, Pt, Pd, Rh, Re, Os, Ag and Au. More preferably M is selected from Ir, Re, Ru, Rh, Ag, Au, Pt, Pd and Cu, wherein Ir and Pt are most preferred.
  • anions X " may be present in the ionic compound of the invention.
  • Suitable anions are in general halides, such as F “ , Cl “ , Br “ or I “ , preferably Br " .
  • a preferred embodiment of the invention is directed to an ionic compound, wherein M of the anionic metal complex is selected from Ir, Ru, Rh, Re, Ag, Au, Pt, Pd and Cu, preferably from Ir and Pt, and the optional further anion X “ is F “ , Cl “ , Br “ or I “ , preferably Br “ .
  • a number of anionic metal complexes of the present invention with a suitable counter cation, preferably a tetraalkylammonium ion, are novel compounds.
  • the present invention further relates also to a compound of the formula (VIII)
  • L 1 is a color emission triggering moiety, comprising bidentate ligands
  • Y is unsubstituted or substituted C-i-C-isalkylene or unsubstituted or substituted
  • Ci-Ci 8 alkyleneoxy optionally interrupted by O or S;
  • X + is a counter cation, preferably N + R 7 R 8 R 9 R 10 , wherein R 7 , R 8 , R 9 , R 10 are the same as R 1 and R 2 ; and the ligand (L 2 - Y-Z " ) is selected from
  • ring A represents an optionally substituted aryl group which may contain a heteroatom
  • ring B represents an optionally substituted nitrogen containing aryl group, which may contain further heteroatoms
  • ring C represents a ligand derived from a nucleophilic carbene, which may contain a heteroatom
  • R 11 is unsubstituted or substituted Ci-C 4 alkyl
  • R 12 is CF 3 or a ring A
  • R 13 is H, unsubstituted or substituted Ci-C 4 alkyl
  • R 14 , R 14 independently are a ring A, unsubstituted or substituted C-i-Csalkyl, Ci-C ⁇ perfluoralkyI or a ring B, unsubstituted or substituted Ci-C 8 alkoxy; and
  • W is N or CH.
  • the linking group Y is Ci-Ci 8 alkylene or CrCi 8 alkyleneoxy, optionally interrupted by O or S,
  • z is 0 or an integer of 1 to 3, more preferably 0 or 1.
  • the anionic group Z " is preferably sulfate (OSO 3 " ) or carboxylate (CO 2 " ), preferably sulfate.
  • Each L 1 of the fragment L 1 M of the metal complex of the present invention independently is a
  • CyC CyC moiety _ ' orrent court consisting of 2 monodentate ligands CyC and/or CyN, or 1 bidentate ligand wherein the 2 moieties CyC and CyN, or CyC and CyC, are interlinked by a chemical bond
  • CyC is an organic moiety containing a carbon atom bonding to M
  • CyN is a cyclic organic moiety containing a nitrogen atom bonding to M.
  • CyN may be a ring B, , as described above for the ligands (L 2 - Y-Z ).
  • 2 rings are interconnected, respectively, to form a bidentate ligand of the formula
  • nucleophilic carbene ligand means typical ⁇ -donor ligands that can substitute classical 2e " donor ligands. They can be cyclic or acyclic. They can have no or several different heteroatoms or several heteroatoms of the same kind.
  • carbenes are, for example, diarylcarbenes, cyclic diaminocarbenes, imidazol-2-ylidenes, imidazolidin- 2-ylidene, 1 ,2,4-triazol-3-yildenes, 1 ,3-thiazol-2-ylidenes, acyclic diaminocarbenes, acyclic aminooxycarbenes, acyclic aminothiocarbenes, cyclic diborylcarbenes, acyclic diborylcarbenes, phosphinosilyl-carbenes, phosphinophosphoniocarbenes, sulfenyl- trifluormethylcarbenes, sulfenylpentafluorothiocarbenes, etc.
  • bidentate ligands of this class include those of the formulae
  • Preferred ligands L 1 comprise at least one ligand of formula wherein ring system A in preferred ligands of this class includes a phenyl group, a substituted phenyl group, a naphthyl group, a substituted naphthyl group, a furyl group, a substituted furyl group, a benzofuryl group, a substituted benzofuryl group, a thienyl group, a substituted thienyl group, a benzothienyl group, a substituted benzothienyl group, and the like.
  • the substitutent on the substituted phenyl group, substituted naphthyl group, substituted furyl group, substituted benzofuryl group, substituted thienyl group, and substituted benzothienyl group include d-C 24 alkyl groups, C 2 -C 24 alkenyl groups, C 2 -C 24 alkynyl groups, aryl groups, heteroaryl groups, d-C 24 alkoxy groups, d-C 24 alkylthio groups, a cyano group, C 2 -C 24 acyl groups, d-C 24 alkyloxycarbonyl groups, a nitro group, halogen atoms, alkylenedioxy groups, and the like.
  • R 16 , R 17 , R 18 , and R 19 are independently of each other hydrogen, d-C 24 alkyl, C 2 -C 24 alkenyl, C 2 -C 24 alkynyl, aryl, heteroaryl, d-C 24 alkoxy, d-C 24 alkylthio, cyano, acyl, alkyloxycarbonyl, a nitro group, or a halogen atom; or two substituents R 16 , R 17 , R 18 , and R 19 , which are adjacent to each other, together form a
  • R 205 , R 206 , R 207 and R 208 are independently of each other H, or
  • the ring A represents an optionally substituted aryl or heteroaryl group; or the ring A may be taken with the pyridyl group binding to the ring A to form a ring; the alkyl group, alkenyl group, alkynyl group, aryl group, heteroaryl group, alkoxy group, alkylthio group, acyl group, and alkyloxycarbonyl group represented by R 16 , R 17 , R 18 , and R 19 may be substituted.
  • Y 3 is S, O, NR 200 , wherein R 200 is hydrogen, d-C 4 alkyl, C 2 -C 4 alkenyl, optionally substituted C 6 -Ci 0 aryl, especially phenyl,
  • X 20 is halogen, especially F, or Cl; hydroxy, cyano, -O-Ci-C 4 alkyl, di(Ci-C 4 alkyl)amino, amino, or cyano; a group -(CH 2 ⁇ 0C(0)(CH 2 )r"CH 3 , wherein r is 1 , or 2, and r" is 0, or 1 ; , -NH-Ph, -
  • Q 1 and Q 2 are independently of each other hydrogen, CrC 24 alkyl, or C 6 -Ci 8 aryl,
  • a V 21 is hydrogen, halogen, d-C 4 alkoxy, or d-C 4 alkyl
  • A is hydrogen, halogen, d-C ⁇ alkoxy, d-C ⁇ alkyl, or C 6 -Ci 0 aryl
  • a V 23 is hydrogen, halogen, d-d 2 alkoxy, d-d 2 alkyl, or C 6 -Ci 0 aryl,
  • A is hydrogen, halogen, d-dalkoxy, or d-dalkyl, or
  • a 22 and A 23 , or A 23 and A 24 together form a group R " , wherein R 205 , R 206 , R 207 and R 208 are independently of each other H, halogen, d-d 2 alkoxy, or d-d 2 alkyl,
  • R is H, halogen, d-d 2 alkyl, CrCi 2 alkoxy, or d-dperfluoroalkyl
  • R 43 is H, halogen, d-d 2 alkyl, d-d 2 alkoxy, Crdperfluoroalkyl, d-Ci 5 aralkyl, or C 6 -Ci 0 aryl
  • R 44 is H, halogen, d-d 2 alkyl, CrCi 2 alkoxy, C 6 -Ci 0 aryl, C 7 -d 5 aralkyl, or d-dperfluoroalkyl
  • R 45 is H, halogen, d-d 2 alkyl, CrCi 2 alkoxy, or d-dperfluoroalkyl, more especially wherein A 21 is hydrogen,
  • a 22 is hydrogen, d-d 2 alkoxy, d-d 2 alkyl, or phenyl
  • a 23 is hydrogen, d-d 2 alkoxy, d-d 2 alkyl, or phenyl
  • a V 24 is hydrogen, or
  • R are independently of each other H, or d-C 8 alkyl
  • R ->43 is H, F, Ci-Ci 2 alkyl, CrC 8 alkoxy, Ci-C 4 perfluoroalkyl, or phenyl
  • R is H, F, Ci-Ci 2 alkyl, CrC 8 alkoxy, or Ci-C 4 perfluoroalkyl, and
  • R ->4 4 5 3 is H, F, Ci-Ci 2 alkyl, Ci-C 8 alkoxy, or C r C 4 perfluoroalkyl.
  • n' is 0, 1 or 2, especially 1 ;
  • a 12 , A 14 , A 16 A 21 , A 22 , A 23 and A 24 are independently of each other hydrogen, CN, halogen,
  • a 23 , A 24 ; or A 18 , A 22 ; or A 23 , A 19 , bonding to vicinal atoms, together are a group of formula
  • a 4J , A 44 , A 4b , A 4b and A 4 ' are independently of each other H, halogen, CN, Ci-C 24 alkyl, Ci-C 24 perfluoroalkyl, Ci-C 24 alkoxy, Ci-C 24 alkylthio, C 6 -Ci 8 aryl, which may optionally be substituted by G 3 , -NR 25 R 26 , -CONR 25 R 26 , or -COOR 27 , or C 2 -Ci 0 heteroaryl; especially , or while each of A 11 , A 13 , A 15 , A' 21 , A' 22 , A' 23 and A' 24 independently is hydrogen or Ci-C 24 alkyl; or 2 adjacent radicals A 11 , A 12 ; A 13 , A 14 ; A 15 , A 16 A' 21 , A 21 ; A' 22 , A 22 ; A' 23 , A 23 ; A' 24 , A 24 , bonding to the same carbon atom
  • E 5 is O, S, or NR 25 ,
  • R 25 and R 26 are independently of each other C 6 -Ci 8 aryl, C 7 -Ci 8 aralkyl, or Ci-C 24 alkyl, R 27 is
  • Ci-C 24 alkyl C 6 -Ci 8 aryl, or C 7 -Ci 8 aralkyl
  • Y 5 , Y 5 and Y 6 are independently of each other a group of formula
  • R 41 is the bond to M
  • R 71 is the bond to M
  • R 42 is hydrogen, or CrC 24 alkyl, CN, Ci-C 24 alkyl, which is substituted by F, halogen, especially F, C 6 -Ci8-aryl, C 6 -Ci 8 -aryl which is substituted by Ci-Ci 2 alkyl, or d-C 8 alkoxy
  • R 43 is hydrogen, CN, halogen, especially F, Ci-C 24 alkyl, which is substituted by F, C 6 -Ci 8 aryl, C 6 -Ci 8 aryl which is substituted by C r Ci 2 alkyl, or C r C 8 alkoxy, -CONR 25 R 26 , -COOR 27 ,
  • E 6 is -S-, -O-, or -NR 25' -, wherein R 25' is C r C 24 alkyl, or C 6 -Ci 0 aryl,
  • R 110 is H, CN, CrC 24 alkyl, CrC 24 alkoxy, C 1 -C 24 alkylthio, -NR 25 R 26 , -CONR 25 R 26 , or -COOR 27 , or R 42 and R 43 are a group of formula , wherein A 41 , A 42 , A 43 , A 44 ,
  • a 45 , A 46 and A 47 are independently of each other H, halogen, CN, d-C 24 alkyl, C r C 24 perfluoroalkyl, CrC 24 alkoxy, CrC 24 alkylthio, C 6 -Ci 8 aryl, which may optionally be substituted by G 3 , -NR 25 R 26 , -CONR 25 R 26 , or -COOR 27 , or C 2 -Ci 0 heteroaryl; especially
  • R 44 is hydrogen, CN or Ci-C 24 alkyl, Ci-C 24 alkyl, which is substituted by F, halogen, especially F, C 6 -Ci8-aryl, C 6 -Ci 8 -aryl which is substituted by CrCi 2 alkyl, or d-C 8 alkoxy
  • R 45 is hydrogen, CN or Ci-C 24 alkyl, Ci-C 24 alkyl, which is substituted by F, halogen, especially F, C 6 -Ci8-aryl, C 6 -Ci 8 -aryl which is substituted by CrCi 2 alkyl, or CrC 8 alkoxy
  • a 11' , A 12' , A 13' , and A 14' are independently of each other H, halogen, CN, C r C 24 alkyl, CrC 24 alkoxy, C r C 24 alkylthio, -NR 25 R 26 , -CONR 25 R 26 , or -COOR 27 , R 68
  • R 16 is hydrogen, halogen, especially F, or Cl; nitro,
  • R 17 is hydrogen, halogen, especially F, or Cl; Ci-C 4 alkyl, Ci-C 4 perfluoroalkyl, optionally substituted C 6 -Ci 0 aryl, especially phenyl, or optionally substituted C 6 -Cioperfluoroaryl, especially C 6 F 5 ,
  • R 18 is hydrogen, Ci-C 4 alkyl, d-C 8 alkoxy, Ci-C 4 perfluoroalkyl, optionally substituted C 6 -Ci 0 aryl, especially phenyl, or optionally substituted C 6 -Ci 0 perfluoroaryl, especially C 6 F 5
  • R 19 is hydrogen, halogen, especially F, or Cl; nitro, cyano, Ci-C 4 alkyl, Ci-C 4 perfluoroalkyl, Ci-C 4 alkoxy, or optionally substituted C 6 -Ci 0 aryl, especially phenyl,
  • a 10 is hydrogen, halogen, especially F, or Cl; nitro, cyano, Ci-C 4 alkyl, C 2 -C 4 alkenyl, Ci-C 4 perfluoroalkyl, -O-Ci-C 4 perfluoroalkyl, tri(Ci-C 4 alkyl)silanyl, especially tri(methyl)silanyl, optionally substituted C 6 -Ci 0 aryl, especially phenyl, or optionally substituted C 6 - Cioperfluoroaryl, especially C 6 F 5 ,
  • a 11 is hydrogen, halogen, especially F, or Cl; nitro, cyano, Ci-C 4 alkyl, C 2 -C 4 alkenyl,
  • a 12 is hydrogen, halogen, especially F, or Cl; nitro, hydroxy, mercapto, amino, Ci-C 4 alkyl, C 2 -C 4 alkenyl, Ci-C 4 perfluoroalkyl, Ci-C 4 alkoxy, OCi-C 4 perfluoroalkyl, -S-Ci-C 4 alkyl, a group -(CH 2 ) r X 20 , wherein r is 1 , or 2, X 20 is halogen, especially F, or Cl; hydroxy, cyano, OCi-C 4 alkyl
  • the basic structure of the group (L 2 - Y- Z " ) may be one of the above-mentioned ligands for L 1 of the groups a) to e) including the mentioned substituents, in particular one of (XX-1 )-(XX- 53) as well as ligands disclosed in WO 2008/098851 , mentioned below, which examples are preferred.
  • the group Y-Z " may be attached at any ring atom of CyC or CyN, at any ring atom of a fused ring or at any ring atom of an aryl or hetaryl substitutent.
  • LDH is a bidentate ligand of formula (XXI).
  • W : ' is selected from O , S, NR 304 , CR 305 R 306 ,
  • X 5 is N or CR 307 ,
  • Q i is selected from O, S, NR 308 ;
  • R, R' and R" independently are selected from Ci-Ci 2 alkyl, C 5 -Ci 0 aryl, C 3 -Ci 2 cycloalkyl, preferably from d-C 6 alkyl, phenyl, cyclopentyl, cyclohexyl; and R may also be hydrogen; or the neighbouring residues R 301 and R 302 form an organic bridging group completing, together with the carbon atoms they are bonding to, a carbocyclic or heterocyclic, non- aromatic or preferably aromatic ring of 5 to 7 ring atoms in total, which optionally may be substituted;
  • R 307 if present, together with its neighbouring residue R 300 forms an organic bridging group completing, with the carbon atoms they are bonding to, a carbocyclic or heterocyclic, non- aromatic or preferably aromatic ring of 5 to 7 ring atoms in total, which optionally may be substituted; and in case that W 5 is O, NR 304 , CR 305 R 306 and/or Q contains a nitrogen atom, R 307 also embraces the meanings given for R 304 ; or R 300 is H, unsubstituted or substituted CrCi 8 alkyl, unsubstituted or substituted C 2 - Ci 8 alkenyl, unsubstituted or substituted C 5 -Ci 0 aryl, unsubstituted or substituted C 2 - Cioheteroaryl, d-Ci 8 acyl; R 308 is hydrogen or a substituent.
  • L 2 which is substituted by a group (Y- Z )
  • Y- Z is a bidentate ligand, which has N, O, P, or S as coordinating atoms and forms 5- or 6-membered rings, when coordinated to metal.
  • Suitable coordinating groups include amino, imino, amido, alkoxide, carboxylate, phosphino, thiolate, and the like.
  • Suitable parent compounds for these ligands include ⁇ -dicarbonyls ( ⁇ -enolate ligands), and their N and S analogs; amino carboxylic acids (aminocarboxylate ligands); pyridine carboxylic acids (iminocarboxylate ligands); salicylic acid derivatives (salicylate ligands); hydroxyquinolines (hydroxyquinolinate ligands) and their S analogs; and diarylphosphinoalkanols (diarylphosphinoalkoxide ligands).
  • R 11 and R 15 are independently of each other hydrogen, CrC 8 alkyl, C 6 -Ci 8 aryl,
  • R 12 and R 16 are independently of each other hydrogen, or d-C 8 alkyl
  • R 13 and R 17 are independently of each other hydrogen, d-C 8 alkyl, C 6 -Ci 8 aryl,
  • R 14 is Ci-C 8 alkyl, C 6 -Ci 0 aryl, or OCuaralkyl,
  • R 19 is Ci-C 8 alkyl
  • R 20 is Ci-C 8 alkyl, or C 6 -Ci 0 aryl,
  • R 21 is hydrogen, d-C 8 alkyl, or Ci-C 8 alkoxy, which may be partially or fully fluorinated,
  • R 22 and R 23 are independently of each other C n (H+F) 2n +i, or C 6 (H+F) 5 , R 24 can be the same or different at each occurrence and is selected from H, or C n (H+F) 2n +i, p is 2, or 3, and
  • R 46 is Ci-C 8 alkyl, C 6 -Ci 8 aryl, or C 6 -Ci 8 aryl, which is substituted by OC 8 alkyl.
  • phosphino alkoxide ligands examples include 3-(diphenylphosphino)-1 -oxypropane [dppO] 1 ,1-bis(trifluoromethyl)-2-(diphenylphosphino)-ethoxide [tfmdpeO].
  • hydroxyquinoline parent compounds can be substituted with groups such as alkyl or alkoxy groups which may be partially or fully fluorinated. In general, these compounds are commercially available.
  • suitable hydroxyquinolinate ligands, L' include: 8-hydroxyquinolinate [8hq] 2-methyl-8-hydroxyquinolinate [Me-8hq] 10-hydroxybenzoquinolinate [10-hbq]
  • anionic metal complexes of the present invention can be prepared from readily available salts of the metals and the ligands as described according to usual methods known from the prior art; see, for example, WO 06/000544 and literature cited therein.
  • Iridium metal complexes of formula lr(L a ) 2 L' can, for example, be prepared by first preparing an intermediate iridium dimer of formula X I
  • the iridium dimers can generally be prepared by first reacting iridium trichloride hydrate with HL a and adding NaX, and by reacting iridium trichloride hydrate with HL a in a suitable solvent, such as 2-ethoxyethanol.
  • Complexes and ligands of the present invention may conveniently be obtained in analogy to methods known in the art, e.g. as initially mentioned.
  • the group Y-Z " is introduced by any conversion of a suitable substituent at a ring atom of the ligands.
  • Another possibility is to introduce the group Y-Z " by any conversion of a suitable substituent at a ring atom of a precursor compound HL', followed by addition to an intermediate dimer
  • Ligands L 1 and the basic structure of L 2 are widely known in the art, many are commercially available.
  • metal complexes having only bidendate ligands are metal complexes having only bidendate ligands.
  • ML 1 is a fragment of a metal complex, wherein L 1 is one bidendate ligand.
  • ML 1 is a fragment of a metal complex, wherein L 1 comprises two bidendate ligands.
  • a particular preferred metal complex, which is employed in the preparation of the ionic dendritic compound is of formula (X)
  • Ci-Ci 8 acyl stands for a radical X'-R 11 , wherein X' is CO or SO 2 and R 11 is selected from monovalent aliphatic or aromatic organic residues, usually from molecular weight up to 300; for example, R 11 may be selected from Ci-Ci 8 alkyl, C 2 -Ci 8 alkenyl, C 5 -Ci 0 aryl which may be unsubstituted or substituted by Ci-C 8 alkyl or halogen or Ci-C 8 alkoxy, C 6 -Ci 5 arylalkyl which may be unsubstituted or substituted in the aromatic part by Ci-C 8 alkyl or halogen or Ci-C 8 alkoxy, C 4 -Ci 2 cycl
  • Acyl is preferably an aliphatic or aromatic residue of an organic acid -CO-R 11 , usually of 1 to 30 carbon atoms, wherein R 11 embraces aryl, alkyl, alkenyl, alkynyl, cycloalkyl, each of which may be substituted or unsubstituted and/or interrupted as described elsewhere inter alia for alkyl residues, or R' may be H (i.e. COR' being formyl).
  • Preferences consequently are as described for aryl, alkyl etc.; more preferred acyl residues are substituted or unsubstituted benzoyl, substituted or unsubstituted Ci-Ci 7 alkanoyl or alkenoyl such as acetyl or propionyl or butanoyl or pentanoyl or hexanoyl, substituted or unsubstituted C 5 -Ci 2 cycloalkylcarbonyl such as cyclohexylcarbonyl.
  • aryl e.g. in Ci-Ci 4 aryl
  • this preferably comprises monocyclic rings or polycyclic ring systems with the highest possible number of double bonds, such as preferably phenyl, naphthyl, anthrachinyl, anthracenyl or fluorenyl.
  • aryl mainly embraces Ci-Ci 8 aromatic moieties, which may be heterocyclic rings (also denoted as heteroaryl) containing, as part of the ring structure, one or more heteroatoms mainly selected from O, N and S; hydrocarbon aryl examples mainly are C 6 -Ci 8 including phenyl, naphthyl, anthrachinyl, anthracenyl, fluorenyl, especially phenyl.
  • Heteroaryl such as C 4 -Ci 8 heteroaryl stands for an aryl group containing at least one heteroatom, especially selected from N, O, S, among the atoms forming the aromatic ring; examples include pyridyl, pyrimidyl, pyridazyl, pyrazyl, thienyl, benzothienyl, pyrryl, furyl, benzofuryl, indyl, carbazolyl, benzotriazolyl, thiazolyl, chinolyl, isochinolyl, triazinyl, tetrahydronaphthyl, thienyl, pyrazolyl, imidazolyl.
  • C 4 -Ci 8 aryl e.g. selected from phenyl, naphthyl, pyridyl, tetrahydronaphthyl, furyl, thienyl, pyrryl, chinolyl, isochinolyl, anthrachinyl, anthracenyl, phenanthryl, pyrenyl, benzothiazolyl, benzoisothiazolyl, benzothienyl, especially C 6 -Ci 0 aryl; most preferred is phenyl, naphthyl.
  • Any arylene is derived from aryl by abstracting a hydrogen atom from any ring carbon atom of the aryl.
  • Halogen denotes I, Br, Cl, F, preferably Cl, F, especially F.
  • Any alkylene is derived from alkyl by abstracting a hydrogen atom from any terminal carbon atom of the alkyl.
  • any alkyl moiety of more than one, especially more than 2 carbon atoms, or such alkyl or alkylene moieties which are part of another moiety may be interrupted by a heterofunction such as O, S, COO, OCNR 10 , OCOO, OCONR 10 , NR 10 CNR 10 , or NR 10 , where R 10 is H, d-C ⁇ alkyl, C 3 -Ci 2 cycloalkyl, phenyl.
  • They can be interrupted by one or more of these spacer groups, one group in each case being inserted, in general, into one carbon-carbon bond, with hetero-hetero bonds, for example O-O, S-S, NH-NH, etc., not occurring; if the interrupted alkyl is additionally substituted, the substituents are generally not ⁇ to the heteroatom. If two or more interrupting groups of the type -O-, -NR 10 -, -S- occur in one radical, they often are identical.
  • alkyl whereever used, thus mainly embraces especially uninterrupted and, where appropriate, substituted Ci-C 22 alkyl such as methyl, ethyl, propyl, isopropyl, n-butyl, sec- butyl, isobutyl, tert-butyl, 2-ethylbutyl, n-pentyl, isopentyl, 1-methylpentyl, 1 ,3-dimethylbutyl, n-hexyl, 1-methylhexyl, n-heptyl, isoheptyl, 1 ,1 ,3,3-tetramethylbutyl, 1-methylheptyl, 3-methylheptyl, n-octyl, 2-ethylhexyl, 1 ,1 ,3-trimethylhexyl, 1 ,1 ,3,3-tetramethylpentyl, nonyl, decyl, undecyl, 1-methylundecyl,
  • Haloalkyl denotes alkyl substituted by halogen; this includes perhalogenated alkyl such as perfluoroalkyl, especially Ci-C 4 perfluoroalkyl, which is a branched or unbranched radical such as for example -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -(CF 2 ) 3 CF 3 , and -C(CF 3 ) 3 .
  • perhalogenated alkyl such as perfluoroalkyl, especially Ci-C 4 perfluoroalkyl, which is a branched or unbranched radical such as for example -CF 3 , -CF 2 CF 3 , -CF 2 CF 2 CF 3 , -CF(CF 3 ) 2 , -(CF 2 ) 3 CF 3 , and -C(CF 3 ) 3 .
  • Aralkyl is, within the definitions given, usually selected from C 7 -C 24 aralkyl radicals, preferably C 7 -Ci 5 aralkyl radicals, which may be substituted, such as, for example, benzyl, 2-benzyl-2- propyl, ⁇ -phenethyl, ⁇ -methylbenzyl, ⁇ , ⁇ -dimethylbenzyl, ⁇ -phenyl-butyl, ⁇ -phenyl-octyl, ⁇ -phenyl-dodecyl; or phenyl-Ci-C 4 alkyl substituted on the phenyl ring by one to three Ci-C 4 alkyl groups, such as, for example, 2-methylbenzyl, 3-methylbenzyl, 4-methylbenzyl, 2,4-dimethylbenzyl, 2,6-dimethylbenzyl or 4-tert-butylbenzyl.or 3-methyl-5-(1 ',1 ',3',3'- t
  • alkenyl whereever used, thus mainly embraces especially uninterrupted and, where appropriate, substituted C 2 -C 22 alkyl such as vinyl, allyl, etc.
  • C 2- C 24 alkynyl is straight-chain or branched and preferably C 2-8 alkynyl, which may be unsubstituted or substituted, such as, for example, ethynyl, 1-propyn-3-yl, 1-butyn-4-yl, 1-pentyn-5-yl, 2-methyl-3-butyn-2-yl, 1 ,4-pentadiyn-3-yl, 1 ,3-pentadiyn-5-yl, 1-hexyn-6-yl, cis-3-methyl-2-penten-4-yn-1 -yl, trans-3-methyl-2-penten-4-yn-1 -yl, 1 ,3-hexadiyn-5-yl, 1-octyn-8-yl, 1-nonyn-9-yl, 1-decyn-10-yl, or 1-tetracosyn-24-yl.
  • Aliphatic cyclic moieties include cycloalkyl, aliphatic heterocyclic moieties, as well as unsaturated variants thereof such as cycloalkenyl.
  • Cycloalkyl such as C 3 -Ci 8 cycloalkyl, is preferably C 3 -Ci 2 cycloalkyl or said cycloalkyl substituted by one to three Ci-C 4 alkyl groups, and includes cyclopropyl, cyclobutyl, cyclopentyl, methylcyclopentyl, dimethylcyclopentyl, cyclohexyl, methylcyclohexyl, dimethylcyclohexyl, trimethylcyclohexyl, tert-butylcyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cyclododecyl, 1-adamantyl, or 2-adamantyl.
  • Cyclohexyl, 1-adamantyl and cyclopentyl are most preferred.
  • C 3 -Ci 2 cycloalkyl includes cyclopropyl, cyclobutyl, cyclopentyl, cyclohexyl, cycloheptyl, cyclooctyl, cyclononyl, cyclodecyl, cycloundecyl, cyclododecyl; preferred among these residues are C 3 -C 6 cycloalkyl as well as cyclododecyl, especially cyclohexyl.
  • heterocyclic aliphatic rings usually containing 5 to 7 ring members, among them at least 1 , especially 1-3, heteromoieties, usually selected from O, S, NR 10 , where R 10 is as explained above for interrupting NR 10 -groups; examples include C 4 -Ci8cycloalkyl, which is interrupted by S, O, or NR 10 , such as piperidyl, tetrahydrofuranyl, piperazinyl and morpholinyl. Unsaturated variants may be derived from these structures by abstraction of a hydrogen atom on 2 adjacent ring members with formation of a double bond between them; an example for such a moiety is cyclohexenyl.
  • R 1 and R 2 together forming a heterocyclic ring are preferably , or corresponding substituted rings.
  • Alkoxy such as Ci-C 24 alkoxy is a straight-chain or branched radical, e.g. methoxy, ethoxy, n- propoxy, isopropoxy, n-butoxy, sec-butoxy, tert-butoxy, amyloxy, isoamyloxy or tert-amyloxy, heptyloxy, octyloxy, isooctyloxy, nonyloxy, decyloxy, undecyloxy, dodecyloxy, tetradecyloxy, pentadecyloxy, hexadecyloxy, heptadecyloxy and octadecyloxy.
  • Any alkyleneoxy is derived from alkoxy by abstracting a hydrogen atom from a carbon atom of the alkyl moiety. If bonding to a heteroatom (e.g. as E 1 in formula (I)), this heteroatom usually is attached to the carbon atom in alkyleneoxy.
  • a heteroatom e.g. as E 1 in formula (I)
  • C 6 -Ci 8 cycloalkoxy is, for example, cyclopentyloxy, cyclohexyloxy, cycloheptyloxy or cyclooctyloxy, or said cycloalkoxy substituted by one to three Ci-C 4 alkyl, for example, methylcyclopentyloxy, dimethylcyclopentyloxy, methylcyclohexyloxy, dimethylcyclohexyloxy, trimethylcyclohexyloxy, or tert-butylcyclohexyloxy.
  • C 6 -C 24 aryloxy is typically phenoxy or phenoxy substituted by one to three Ci-C 4 alkyl groups, such as, for example o-, m- or p-methylphenoxy, 2,3-dimethylphenoxy, 2,4-dimethylphenoxy, 2,5-dimethylphenoxy, 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3,5-dimethylphenoxy, 2-methyl-6-ethylphenoxy, 4-tert-butylphenoxy, 2-ethylphenoxy or 2,6-diethylphenoxy.
  • Ci-C 4 alkyl groups such as, for example o-, m- or p-methylphenoxy, 2,3-dimethylphenoxy, 2,4-dimethylphenoxy, 2,5-dimethylphenoxy, 2,6-dimethylphenoxy, 3,4-dimethylphenoxy, 3,5-dimethylphenoxy, 2-methyl-6-ethylphenoxy, 4-tert-butylphenoxy, 2-ethy
  • C 6 -C 24 aralkoxy is typically phenyl-Ci-C 9 alkoxy, such as, for example, benzyloxy, ⁇ -methylbenzyloxy, ⁇ , ⁇ -dimethylbenzyloxy or 2-phenylethoxy.
  • Ci-C 24 alkylthio radicals are straight-chain or branched alkylthio radicals, such as e.g. methylthio, ethylthio, propylthio, isopropylthio, n-butylthio, isobutylthio, pentylthio, isopentyl- thio, hexylthio, heptylthio, octylthio, decylthio, tetradecylthio, hexadecylthio or octadecylthio.
  • SiIyI such as SiRR'R" is preferably Si substituted by two or preferably three moieties selected from unsubstituted or substituted hydrocarbyl or hydrocarbyloxy (wherein the substituents are preferably other than substituted silyl), as defined above, or by unsubstituted or substituted heteroaryl.
  • the silyl group is of the type -SiH(R 400 ) with R 40 O preferably being hydrocarbyl or hydrocarbyloxy.
  • Preferred hydrocarbyl(oxy) are CrC 2 oalkyl(oxy), phenyl(oxy), CrC 9 alkylphenyl(oxy).
  • three CrC 2 oalkyl or Ci-C 2 oalkoxy substituents i.e. substituted silyl then is Si(R 401 )3 with R 401 being d-C 2 oalkyl or CrC 2 oalkoxy, especially three Ci-C 8 -alkyl substitutents, such as methyl, ethyl, isopropyl, t-butyl or isobutyl.
  • the number of negative charges, i.e. of the metal complex and the optionally further anion(s) X ⁇ , in the ionic compound of the present invention equals the number of ammonium groups in the dendrimer.
  • the ionic compounds of the present invention are prepared by a biphasic
  • reaction is carried out between equimolar amounts of the halide salts of the dendrimers NCN ⁇ 2G 1-3 ⁇ or the corresponding Si-compounds Si[NCN ⁇ 2G 1-3 ⁇ ] 4 and
  • Further cations such as alkali cations, may be used as counterions of the complex educt as well.
  • the reaction may be carried out as a two-phase reaction, preferably with the dendrimer educt in the aqueous phase, or as a homogenous phase reaction, e.g. in water or polar solvents, such as alcohols, or mixtures thereof.
  • the ion exchange step can be followed by a desalination step. Further details of the preferred preparation method can be found in section (B) of the examples.
  • an electronic device comprising the ionic host guest dendritic compounds of formula (II) and its fabrication process.
  • the electronic device can comprise at least one organic active material positioned between two electrical contact layers, wherein at least one of the layers of the device includes the ionic dendritic compound.
  • the electronic device can comprise an anode layer (a), a cathode layer (e), and an active layer (c). Adjacent to the anode layer (a) is an optional hole-injecting/transport layer (b), and adjacent to the cathode layer (e) is an optional electron-injection/transport layer (d). Layers (b) and (d) are examples of charge transport layers.
  • the active layer (c) can comprise at least approximately 1 weight percent of the ionic dendritic compound of the present invention.
  • the active layer (c) may be substantially 100% of the ionic dendriticic compound because a host charge transporting material, such as AIq 3 is not needed.
  • substantially 100% it is meant that the ionic dendritic compound is the only material in the layer, with the possible exception of impurities or adventitious by-products from the process to form the layer.
  • the ionic dendritic compound may be a dopant within a host material, which is typically used to aid charge transport within the active layer (c).
  • the active layer (c) may include an additional other luminescent material, for example a luminescent metal complex.
  • the device may include a support or substrate adjacent to the anode layer (a) or the cathode layer (e). Most frequently, the support is adjacent the anode layer (a).
  • the support can be flexible or rigid, organic or inorganic. Generally, glass or flexible organic films are used as a support.
  • the anode layer (a) is an electrode that is more efficient for injecting holes compared to the cathode layer (e).
  • the anode can include materials containing a metal, mixed metal, alloy, metal oxide or mixed-metal oxide. Suitable metal elements within the anode layer (a) can include the Groups 4, 5, 6, and 8-1 1 transition metals.
  • anode layer (a) is to be light-transmitting
  • mixed-metal oxides of Groups 12, 13 and 14 metals such as indium-tin-oxide
  • materials for anode layer (a) include indium-tin-oxide ("ITO"), aluminum-tin-oxide, gold, silver, copper, nickel, and selenium.
  • the anode layer (a) may be formed by a chemical or physical vapor deposition process or spin-cast process. Chemical vapor deposition may be performed as a plasma-enhanced chemical vapor deposition ("PECVD”) or metal organic chemical vapor deposition (“MOCVD”).
  • PECVD plasma-enhanced chemical vapor deposition
  • MOCVD metal organic chemical vapor deposition
  • Physical vapor deposition can include all forms of sputtering (e. g., ion beam sputtering), e- beam evaporation, and resistance evaporation.
  • physical vapor deposition examples include rf magnetron sputtering or inductively- coupled plasma physical vapor deposition ("ICP- PVD"). These deposition techniques are well-known within the semiconductor fabrication arts.
  • a hole-transport layer (b) may be adjacent to the anode. Both hole transporting small molecule compounds and polymers can be used. Commonly used hole transporting molecules include: 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-diphenylaminostyrene (TPS
  • hole transporting polymers are polyvinylcarbazole, (phenylmethyl) polysilane, poly(3,4-ethylendioxythiophene) (PEDOT), and polyaniline.
  • Hole-transporting polymers can be obtained by doping hole-transporting molecules such as those mentioned above into polymers such as polystyrene and polycarbonate.
  • the hole-injection/transport layer (b) can be formed using any conventional means, including spin-coating, casting, and printing, such as gravure printing.
  • the layer can also be applied by ink jet printing, thermal patterning, or chemical or physical vapor deposition.
  • the anode layer (a) and the hole-injection/transport layer (b) are patterned during the same lithographic operation.
  • the pattern may vary as desired.
  • the layers can be formed in a pattern by, for example, positioning a patterned mask or resist on the first flexible composite barrier structure prior to applying the first electrical contact layer material.
  • the layers can be applied as an overall layer (also called blanket deposit) and subsequently patterned using, for example, a patterned resist layer and wet-chemical or dry-etching techniques. Other processes for patterning that are well known in the art can also be used.
  • the anode layer (a) and hole injection/transport layer (b) typically are formed into substantially parallel strips having lengths that extend in substantially the same direction.
  • the active layer (c) comprises the ionic dendritic compound of the present invention.
  • the particular material chosen may depend on the specific application, potentials used during operation, or other factors.
  • the active layer (c) may comprise a host material capable of transporting electrons and/or holes, doped with an emissive material that may trap electrons, holes, and/ or excitons, such that excitons relax from the emissive material via a photoemissive mechanism.
  • Active layer (c) may comprise a single material that combines transport and emissive properties. Whether the emissive material is a dopant or a major constituent, the active layer may comprise other materials, such as dopants that tune the emission of the emissive material.
  • Active layer (c) may include a plurality of emissive materials capable of, in combination, emitting a desired spectrum of light.
  • phosphorescent emissive materials include the ionic dendritic compounds of the present invention.
  • fluorescent emissive materials include DCM and DMQA.
  • host materials include AIq 3 , CBP and mCP. Examples of emissive and host materials are disclosed in US 6,303,238 B, which is incorporated by reference in its entirety.
  • Examples of methods for forming the active layer (c) include deposition by solution processing.
  • Examples of film-forming methods from a solution include application methods, such as spin-coating, casting, microgravure coating, roll-coating, wire bar-coating, dip- coating, spray-coating, screen-printing, flexography, offset-printing, gravure printing and ink- jet-printing.
  • composition used for forming the active layer (c) at least one kind of the ionic dendritic compounds of the present invention and at least one solvent are contained, and additives, such as hole transport material, electron transport material, luminescent material, rheology modifier or stabilizer, may be added.
  • additives such as hole transport material, electron transport material, luminescent material, rheology modifier or stabilizer.
  • the amount of solvent in the composition is 1 to 99 wt% of the total weight of the composition and preferably 60 to 99 wt% and more preferably 80 to 99 wt%.
  • the solvent used in the solution processing method is not particularly limited and preferable are those which can dissolve or uniformly disperse the materials.
  • the materials may be dissolved in a solvent, the solution deposited onto a substrate, and the solvent removed to leave a solid film.
  • Any suitable solvents may be used to dissolve the ionic compounds, provided it is inert, may dissolve at least some material and may be removed from the substrate by conventional drying means (e.g. application of heat, reduced pressure, airflow, etc.).
  • Suitable organic solvents include, but are not limited to, are aromatic or aliphatic hydrocarbons, halogenated such as chlorinated hydrocarbons, esters, ethers, ketones, amide, such as chloroform, dichloroethane, tetrahydrofuran, toluene, xylene, ethyl acetate, butyl acetate, methyl ethyl ketone, acetone, dimethyl formamide, dichlorobenzene, chlorobenzene, propylene glycol monomethyl ether acetate (PGMEA), and alcohols, and mixtures thereof. Also water and mixtures with water miscible solvents are possible.
  • halogenated such as chlorinated hydrocarbons, esters, ethers, ketones, amide, such as chloroform, dichloroethane, tetrahydrofuran, toluene, xylene, ethyl acetate, butyl acetate, methyl e
  • Optional layer (d) can function both to facilitate electron injection/transport, and also serve as a buffer layer or confinement layer to prevent quenching reactions at layer interfaces. More specifically, layer (d) may promote electron mobility and reduce the likelihood of a quenching reaction if layers (c) and (e) would otherwise be in direct contact.
  • materials for optional layer (d) include metal-chelated oxinoid compounds (e. g., tris(8- hydroxyquinolato)aluminum (AIq 3 ) or the like); phenanthroline-based compounds (e.
  • optional layer (d) may be inorganic and comprise BaO, LiF, Li 2 O, or the like.
  • the electron injection/transport layer (d) can be formed using any conventional means, including spin-coating, casting, and printing, such as gravure printing.
  • the layer can also be applied by ink jet printing, thermal patterning, or chemical or physical vapor deposition.
  • the cathode layer (e) is an electrode that is particularly efficient for injecting electrons or negative charge carriers.
  • the cathode layer (e) can be any metal or nonmetal having a lower work function than the first electrical contact layer (in this case, the anode layer (a)).
  • Materials for the second electrical contact layer can be selected from alkali metals of Group 1 (e. g., Li, Na, K, Rb, Cs), the Group 2 (alkaline earth) metals, the Group 12 metals, the rare earths, the lanthanides (e. g. , Ce, Sm, Eu, or the like), and the actinides.
  • Materials, such as aluminum, indium, calcium, barium, yttrium, and magnesium, and combinations thereof, may also be used.
  • Li-containing organometallic compounds, LiF, and Li 2 O can also be deposited between the organic layer and the cathode layer to lower the operating voltage.
  • Specific non- limiting examples of materials for the cathode layer (e) include barium, lithium, cerium, cesium, europium, rubidium, yttrium, magnesium, or samarium.
  • the cathode layer (e) is usually formed by a chemical or physical vapor deposition process. In general, the cathode layer will be patterned, as discussed above in reference to the anode layer (a) and optional hole injecting layer (b). If the device lies within an array, the cathode layer (e) may be patterned into substantially parallel strips, where the lengths of the cathode layer strips extend in substantially the same direction and substantially perpendicular to the lengths of the anode layer strips.
  • Pixels are formed at the cross points (where an anode layer strip intersects a cathode layer strip when the array is seen from a plan or top view).
  • additional layer(s) may be present within organic electronic devices.
  • a layer (not shown) between the hole injecting layer (b) and the active layer (c) may facilitate positive charge transport, band-gap matching of the layers, function as a protective layer, or the like.
  • additional layers between the electron injecting layer (d) and the cathode layer (e) may facilitate negative charge transport, band-gap matching between the layers, function as a protective layer, or the like.
  • Layers that are known in the art can be used. Some or all of the layers may be surface treated to increase charge carrier transport efficiency. The choice of materials for each of the component layers may be determined by balancing the goals of providing a device with high device efficiency with the cost of manufacturing, manufacturing complexities, or potentially other factors.
  • the materials of the charge transport layers (b) and (d) are generally of the same type as the materials of the active layer (c). More specifically, if the active layer (c) has a small molecule compound, then the charge transport layers (b) and (d), if either or both are present, can have a different small molecule compound. If the active layer (c) has a polymer, the charge transport layers (b) and (d), if either or both are present, can also have a different polymer. Still, the active layer (c) may be a small molecule compound, and any of its adjacent charge transport layers may be polymers.
  • Each functional layer may be made up of more than one layer.
  • the cathode layer may comprise a layer of a Group I metal and a layer of aluminum.
  • the Group I metal may lie closer to the active layer (c), and the aluminum may help to protect the Group I metal from environmental contaminants, such as water.
  • the different layers may have the following range of thicknesses: inorganic anode layer (a), usually no greater than approximately 500 nm, for example, approximately 50-200 nm; optional hole-injecting layer (b), usually no greater than approximately 100 nm, for example, approximately 50-200 nm; active layer (c), usually no greater than approximately 100 nm, for example, approximately 10-80 nm; optional electron- injecting layer (d), usually no greater than approximately 100 nm, for example, approximately 10-80 nm; and cathode layer (e), usually no greater than approximately 1000 nm, for example, approximately 30-500 nm. If the anode layer (a) or the cathode layer (e) needs to transmit at least some light, the thickness of such layer may not exceed approximately 100 nm.
  • the location of the electron-hole recombination zone in the device, and thus the emission spectrum of the device, can be affected by the relative thickness of each layer.
  • a potential light emitting compound such as AIq 3
  • the electron-hole recombination zone can lie within the AIq 3 layer.
  • the thickness of the electron-transport layer should be chosen so that the electron-hole recombination zone lies within the light emitting layer (i.e., active layer (c)).
  • the desired ratio of layer thicknesses can depend on the exact nature of the materials used.
  • the efficiency of the devices made with metal complexes can be further improved by optimizing the other layers in the device.
  • more efficient cathodes such as Ca, Ba, Mg/Ag, or LiF/AI can be used.
  • Shaped substrates and hole transport materials that result in a reduction in operating voltage or increase quantum efficiency are also applicable.
  • Additional layers can also be added to tailor the energy levels of the various layers and facilitate electroluminescence.
  • the active layer (c) can be a light emitting layer that is activated by a signal (such as in a light emitting diode) or a layer of material that responds to radiant energy and generates a signal with or without an applied potential (such as detectors or voltaic cells).
  • a signal such as in a light emitting diode
  • a layer of material that responds to radiant energy and generates a signal with or without an applied potential (such as detectors or voltaic cells).
  • Examples of electronic devices that may respond to radiant energy are selected from photoconductive cells, photoresistors, photoswitches, phototransistors, and phototubes, and photovoltaic cells.
  • the electroluminescent devices may be employed for full color display panels in, for example, mobile phones, televisions and personal computer screens. Accordingly the present invention relates also to a device selected from stationary and mobile displays, such as displays for computers, mobile phones, laptops, pdas, TV sets, displays in printers, kitchen equipment, billboards, lightings, information boards and destination boards in trains and buses, containing an organic light emitting diode according to the present invention.
  • stationary and mobile displays such as displays for computers, mobile phones, laptops, pdas, TV sets, displays in printers, kitchen equipment, billboards, lightings, information boards and destination boards in trains and buses, containing an organic light emitting diode according to the present invention.
  • OLEDs electrons and holes, injected from the cathode (e) and anode (a) layers, respectively, into the photoactive layer (c), form negative and positively charged polarons in the active layer (c). These polarons migrate under the influence of the applied electric field, forming a polaron exciton with an oppositely charged species and subsequently undergoing radiative recombination.
  • a sufficient potential difference between the anode and cathode usually less than approximately 20 volts, and in some instances no greater than approximately 5 volts, may be applied to the device. The actual potential difference may depend on the use of the device in a larger electronic component.
  • the anode layer (a) is biased to a positive voltage and the cathode layer (e) is at substantially ground potential or zero volts during the operation of the electronic device.
  • a battery or other power source (s) may be electrically connected to the electronic device as part of a circuit.
  • the compound does not need to be in a solid matrix diluent (e. g., host charge transport material) when used in layer (b) (c), or (d) in order to be effective.
  • a layer greater than approximately 1 % by weight of the metal complex compound, based on the total weight of the layer, and up to substantially 100% of the complex compound can be used as the active layer (c).
  • Additional materials can be present in the active layer (c) with the complex compound. For example, a fluorescent dye may be present to alter the color of emission.
  • a diluent may also be added.
  • the diluent can be a polymeric material, such as poly (N-vinyl carbazole) and polysilane. It can also be a small molecule, such as 4,4'-N,N'-dicarbazole biphenyl or tertiary aromatic amines.
  • the complex compound is generally present in a small amount, usually less than 20% by weight, preferably less than 10% by weight, based on the total weight of the layer.
  • the ionic dendritic compounds may be used in applications other than electronic devices. For example, they may be used as catalysts or indicators (e. g., oxygen-sensitive indicators, phosphorescent indicators in bioassays, or the like).
  • UV-VIS Varian CARY 50 Scan UV-VIS spectrophotometer; room temperature; dichloromethane as solvent.
  • the obtained pyridinium salt is dissolved in 10 ml of dichloromethane, the solution is added to a solution of 1 g of tetra-n-butylammonium chloride in 50 ml of deionised water and the biphasic system is stirred for 16 hours. The organic layer is separated, washed with water, dried, concentrated and recrystallised from diethyl ether to obtain 5 as a bright yellow powder.
  • a solution of 0.54 g (0.83 mmol) of 4 in 25 ml of DMF is stirred at 0 0 C for 30 minutes, followed by adding 0.022 g (0.91 mmol) of sodium hydride.
  • the resulting black suspension is stirred at room temperature for 16 hours.
  • 0.123 g (0.001 mol) of 1 ,3-dioxithiolane-2,2-dioxide are subsequently added and the resulting orange solution is stirred for 12 hours.
  • the solution is concentrated to 2 ml and the resulting reddish mixture is slowly added to diethyl ether resulting in a yellow solid which is collected by filtration.
  • the solid is dissolved in 20 ml of dichloromethane, the solution is added to a solution of 0.664 g of tetra-n-butylammonium chloride in 40 ml of deionised water and the biphasic system is stirred for 16 hours. The organic layer is separated, washed with water, dried and concentrated. The remaining solution is added slowly to diethyl ether and the obtained yellow precipitate is collected by filtration to obtain 6.
  • Organic luminescence device structure On a glass substrate the following layers are superimposed: ITO, PEDOT, the electroluminescent composition according in Table 2 is spin-coated from a solution of chlorobenzene, finally barium and aluminum.
  • Table 3 shows color data (CIE-data x, y) and efficacy when the device is driven to emit 100cd/sqm luminance, and corresponding current density and voltage.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention porte sur de nouveaux composés hôte-invité ioniques électroluminescents, notamment des émetteurs phosphorescents organométalliques anioniques noyés dans une espèce dendritique cationique, sur des dispositifs électroniques comprenant les composés ioniques électroluminescents et sur leur utilisation dans des dispositifs électroniques, notamment des diodes électroluminescentes organiques (OLED). Le composé ionique d'un dendrimère cationique et d'un complexe métallique ayant un substituant anionique est caractérisé par le fait que la fraction dendrimère contient au moins 1, de préférence 2 à 24, unités structurales cationiques.
PCT/EP2008/068224 2008-01-04 2008-12-23 Matières dendritiques hôte-invité ioniques électroluminescentes Ceased WO2009087064A1 (fr)

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Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102559169A (zh) * 2011-12-21 2012-07-11 湘潭大学 树枝状三核环金属铂配合物电致磷光材料及其在聚合物电致白光器件中的应用

Citations (2)

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WO2006097717A1 (fr) * 2005-03-15 2006-09-21 Isis Innovation Limited Dendrimeres fortement ramifies
US20070114915A1 (en) * 2003-11-25 2007-05-24 Merck Patent Gmbh Organic electroluminescent element

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Publication number Priority date Publication date Assignee Title
US20070114915A1 (en) * 2003-11-25 2007-05-24 Merck Patent Gmbh Organic electroluminescent element
WO2006097717A1 (fr) * 2005-03-15 2006-09-21 Isis Innovation Limited Dendrimeres fortement ramifies

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VAN DE COEVERING R, ALFERS A, MEELDIJK J, MARTÍNEZ-VIVIENTE E, PREGOSIN P, KLEIN GEBBINK R, VAN KOTEN G: "Ionic Core-Shell Dendrimers with an Octacationic Core as Noncovalent Supports for Homogeneous Catalysts", JOURNAL OF THE AMERICAN CHEMICAL SOCIETY, vol. 128, 2001, pages 12700 - 12713, XP002480496 *

Cited By (1)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
CN102559169A (zh) * 2011-12-21 2012-07-11 湘潭大学 树枝状三核环金属铂配合物电致磷光材料及其在聚合物电致白光器件中的应用

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