WO2016037888A1 - Composé complexe métallique à solubilité amélioré - Google Patents

Composé complexe métallique à solubilité amélioré Download PDF

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WO2016037888A1
WO2016037888A1 PCT/EP2015/069891 EP2015069891W WO2016037888A1 WO 2016037888 A1 WO2016037888 A1 WO 2016037888A1 EP 2015069891 W EP2015069891 W EP 2015069891W WO 2016037888 A1 WO2016037888 A1 WO 2016037888A1
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radical
metal complex
substituted
branched
unsubstituted
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PCT/EP2015/069891
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Andreas Jacob
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Cynora Gmbh
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    • 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
    • C07F1/00—Compounds containing elements of Groups 1 or 11 of the Periodic Table
    • C07F1/08—Copper 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
    • H01—ELECTRIC ELEMENTS
    • H01L—SEMICONDUCTOR DEVICES NOT COVERED BY CLASS H10
    • H01L31/00—Semiconductor devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation and specially adapted either for the conversion of the energy of such radiation into electrical energy or for the control of electrical energy by such radiation; Processes or apparatus specially adapted for the manufacture or treatment thereof or of parts thereof; Details thereof
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/361—Polynuclear complexes, i.e. complexes comprising two or more metal centers
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/371—Metal complexes comprising a group IB metal element, e.g. comprising copper, gold or silver
    • 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
    • C09K2211/1003—Carbocyclic compounds
    • C09K2211/1007—Non-condensed systems
    • 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
    • C09K2211/188—Metal complexes of other metals not provided for in one of the previous groups
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the present invention relates to metal complex compounds MK, having a structure of the formula (I),
  • the carbon atoms C 1 and C 2 are part of a mononuclear, aromatic or heteroaromatic ring system F 1 having a total of up to 6 carbon atoms, the ring system F 1 being substituted by R 5 .
  • the invention also relates to the preparation of the compounds MK.
  • the present invention comprises an optically active layer S and an optoelectronic device comprising a metal complex compound MK according to the invention and a method for producing such an optoelectronic device and for generating light therewith.
  • an organic ligand OL suitable for producing a metal complex compound MK according to the invention is included.
  • optically active materials used here are introduced into the optically active layer (light-emitting or absorbing layer) of the corresponding opto-electronic device.
  • metal complex compounds have been found which have desired optical properties.
  • metal complex compounds are known which have an emission maximum in the wavelength range between approximately 400 and 800 nm which is visible to the human eye and can easily be excited by applying an electric current in order to emit light of high quantum efficiency and quantum intensity.
  • the metal complex compounds shown in WO 2013/014066 with a nitrogen donor and a phosphorus donor proved to be advantageous in terms of their optical properties.
  • the metal complex compounds shown in WO 2013/014066 are difficult to dissolve in many common organic solvents such as benzene or toluene and are prone to undesirable crystallization. This leads to the formation of undesired crystalline regions in optically active layers and reduces the usability in optoelectronic devices.
  • halogenated solvents such as chlorobenzene, dichlorobenzene or dichloromethane a certain solubility is given, which is technically and toxicologically problematic due to the halogen content.
  • a first aspect of the present invention relates to a metal complex compound MK having a structure of the formula (I):
  • carbon atoms C 1 and C 2 are part of a mononuclear, aromatic or heteroaromatic ring system F 1 having a total of up to 6 carbon atoms, the ring system F 1 being substituted by R 5 ;
  • N represents a nitrogen atom
  • P represents a phosphorus atom
  • R 1 and R 2 are each an atom or a radical independently selected from the group consisting of -R a , -OR a , -SR a , -C (O) -R a , -C (O) -OR a , - OC (O) -R a , -NH-R a , -NR a R b , -R a -NC (O) -R b , -Si (R a ) x (OR b ) 3 -x, hydrogen and halogen wherein R a and R b are each an aryl, heteroaryl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkenyl, heterocycloalkenyl, heteroalkynyl , Cycloalky
  • Heteroalkylcycloalkyl, Heteroalkylcycloalkenyl-, Heteroalkylcycloalkinyl-, Heteroalkenylcycloalkenyl-, Heteroalkenylcycloalkinyl-, Heteroalkinylcycloalkenyl-, Heteroalkinylcycloalkinyl-, aralkyl or heteroaralkyl radical having up to 40 carbon atoms and may each be unsubstituted or substituted, wherein x 1, 2 or 3 ; R 3 and R 4 are each independently selected from the group consisting of an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkenyl, heterocycloalkenyl, heteroalkynyl -, Cycloalkinyl-, Hetero
  • R 5 is selected from the group consisting of -R c -NR d R e, halo, -R f, -NR g R h, - R c -NR g R h, -OR c -R g -R c -SR g , -R c -C (O) -R g , -R c -C (O) -R g , -R c -OC (O) -R g , -C (O) -OR g , -R c -SiR d R e R g , -R c -SiR g R h R i , -R c -SO-R g , -R c -SO 2 -R g , -R c -PO 4 R d R e R g , -R c -PO 4 R d R e R g
  • R c is an unbranched or branched alkylene radical, an unbranched or branched heteroalkylene radical, a straight or branched alkenylene radical, a straight or branched heteroalkenylene radical, a straight or branched alkynylene radical or a straight or branched heteroalkynylene radical each having up to 40 carbon atoms and may each be unsubstituted or substituted or R c is a covalent bond,
  • R d and R e are connected unbranched or branched alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene, or heteroalkynylene radicals which, together with the radical to which they are attached, are a heterocycloalkyl, heteroaryl, heterocycloalkenyl form - or heterocycloalkinyl radical having up to 10 carbon atoms and may each be unsubstituted or substituted, wherein R f is a branched or unbranched alkyl radical, an alkyl heterocycloalkyl radical, a heterocycloalkyl radical, a cycloalkyl radical, an unbranched or branched alkenyl radical, a cycloalkenyl radical, an unbranched or branched alkynyl radical, a cycloalkynyl radical, an aryl radical, an alkylcycloalkyl radical, an unbranched or branched heteroalkyl radical,
  • R 5 is not H, so that the aromatic or heteroaromatic ring system F 1 is substituted. As a result, the symmetry of the structure of the metal complex compound MK and thus its crystallization tendency can be reduced.
  • R 5 is a halogen (especially F, Cl, Br or I), an alkoxy radical (eg a methoxy or ethoxy radical), a branched alkyl radical (eg a - C (CH 3 ) 3 ) or a Radical of the formula (XV):
  • F 2 together with the N is a heterocycloalkyl, heteroaryl, heterocycloalkenyl or heterocycloalkynyl radical having up to 10 carbon atoms is unsubstituted or substituted, in particular together with the N is piperidinyl, and
  • R c is as defined above, preferably an alkyl radical having up to 5 carbon atoms, in particular methylene (-CH 2 -) represents.
  • the metal complex compounds MK according to the invention are preferably more readily soluble in organic solvents, such as, for example, benzene or toluene. This opens the possibility to print on any substrate with such a metal complex compounds MK.
  • Alkenyl, heteroalkenyl, cycloalkenyl and heterocycloalkenyl radicals may each contain one or more than one double bond.
  • Alkynyl, heteroalkynyl, cycloalkynyl and heterocycloalkynyl radicals may each contain one or more than one triple bond.
  • the radicals can each be linear or branched. In particular, alkyl and heteroalkyl radicals may be linear or branched.
  • heteromatic ring system is to be understood herein in the broadest sense as meaning that one or more carbon atoms C or CH groups in the aromatic ring system are each replaced by a heteroatom (hence carbon) Carbon atoms C or CH groups in the aromatic ring system may be replaced by N, O, S, P.
  • heteroaryl radical or "heteroararyl radical” are to be understood herein in the broadest sense as an aryl radical or araryl radical in which one or more carbon atoms C or CH groups in the aromatic ring system each by a Heteroatom (therefore not carbon) is / are replaced.
  • one or more carbon atoms C or CH groups in the aromatic ring system may be replaced by N, O, S, P.
  • heteroarylene or "heteroararylene radicals A (hetero) aryl or (hetero) araryl can be mononuclear or polynuclear.
  • heteroalkyl radical or “heterocycloalkyl radical” are to be understood herein in the broadest sense as an alkyl radical or cycloalkyl radical in which each one or more herein contained (s) -CH 2 - is replaced by a heteroatom (therefore not carbon) or a functional group.
  • R 6 and R 7 are each independently selected from the group consisting of hydrogen, halogen, an alkyl
  • heteroalkenylene or heterocycloalkenylene radicals are to be understood herein in the broadest sense as an alkynyl radical or cycloalkynyl radical in which one or more of the (s) -CH 2 - or -C (s) contained therein is in each case ⁇ C- is replaced by a heteroatom (therefore not carbon) or a functional group.
  • Heteroalkenylcycloalkinyl-, a Heteroalkinylcycloalkenyl- and a Heteroalkinylcycloalkinyl- radical in which one or more of -CH 2 -, -CH CH- or -C ⁇ C- may be replaced by one of the above groups, respectively.
  • heteroalkylcycloalkylene radical heteroalkylcycloalkenylene radical, a heteroalkylcycloalkynylene radical, a heteroalkenylcycloalkenylene radical, a heteroalkenylcycloalkynylene radical, a heteroalkynylcycloalkenylene radical and a heteroalkynylcycloalkynylene radical.
  • All organic radicals here may be substituted or unsubstituted.
  • Substituted means that one, two or more hydrogens are replaced by one or more heteroatoms.
  • a functional group can thereby be obtained. This may be selected, for example, from: -OH, OO, -SH, SS, -SO 2 , -OOH, -F, -Cl, -Br, -I, -NR a R b or -ONR a , where R a and R b may each independently be selected from the group consisting of hydrogen, halogen, an alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkylcycloalkyl, Aryl, heteroaryl, aralkyl and heteroaralkyl radical having up to 40 carbon atoms.
  • the ring system F 1 may be any mononuclear aromatic or heteroaromatic ring system F 1 having a total of up to 6 carbon atoms which includes the carbon atoms C 1 and C 2 . According to a preferred embodiment, F 1 is a mononuclear aromatic or heteroaromatic ring system F 1 from a total of 5 or 6 atoms.
  • the aromatic or heteroaromatic ring system F 1 consists of atoms selected from the group consisting of C, N, O and S. Even more preferably, the ring system F 1 consists only of carbon atoms.
  • F 1 is a phenyl substituted with R 5 .
  • F 1 is a phenyl ring which is substituted in the para position to the nitrogen atom N with R 5 .
  • the nitrogen atom N corresponds to the N shown in formula (I).
  • the radicals R 1 and R 2 may be different or similar.
  • R 1 and R 2 are each independently a substituted or unsubstituted aryl radical.
  • R 1 and R 2 are each independently an unsubstituted phenyl radical or a phenyl radical substituted in the para position to the bond to the phosphorus atom with an electron acceptor radical or an electron donor radical.
  • R 1 and R 2 are both identical and each is an unsubstituted phenyl radical or a phenyl radical substituted in the para position to the bond to the phosphorus atom with an electron acceptor radical or an electron donor radical.
  • An electron acceptor moiety is to be understood in the broadest sense as any moiety capable of accepting electrons.
  • An electron-donor radical is to be understood in the broadest sense as a any residue capable of donating electrons.
  • such a radical may be an alkoyl radical (eg a methoxy or ethoxy radical), a halide radical (eg F, Cl, Br, I) or a haloalkyl radical (eg -CF 3 ).
  • R 5 according to formula (I) is not H, so that F 1 is substituted.
  • R 5 is selected from the group consisting of a halogen, a -CH 2 -heterocycloalkyl radical, an unsubstituted or substituted branched alkyl radical, an unsubstituted or substituted unbranched alkyl radical, an unsubstituted or substituted branched heteroalkyl Radical and an unsubstituted or substituted unbranched heteroalkyl radical each having up to 20 carbon atoms.
  • R 5 is preferably selected from one of the abovementioned radicals and bonded to F 1 in the para position to the nitrogen N.
  • R 5 has not more than 15 carbon atoms, more preferably not more than 10 carbon atoms, even more preferably not more than 8 carbon atoms, even more preferably not more than 7 carbon atoms, especially not more than 6 carbon atoms.
  • R 5 is -CH 2 -pipehdyl, a halogen (preferably F, I or Br, in particular F), or an unsubstituted branched alkyl radical having up to 10 carbon atoms.
  • the radical R 5 is bonded to F 1 in the para position to the nitrogen N and is -CH 2 -piperidyl, a halogen (preferably F, I or Br, in particular F), or an unsubstituted alkyl radical with bis to 10 carbon atoms.
  • R 5 may also be a charge transfer group (CTG) for transporting holes or electrons, wherein the charge-transporting group preferably has an aryl or heteroaryl moiety which preferably contains one or more N, O, or C groups. , S, and / or P atoms or a Combination of this has.
  • CCG charge transfer group
  • the charge-transporting group may be one as described in WO 201 1/064335.
  • the charge-transporting group may be a substituted or unsubstituted diarylamine, a substituted or unsubstituted arylamine, a substituted or unsubstituted carbazole, a substituted or unsubstituted thiophene, a substituted or unsubstituted pyrrole, a substituted or unsubstituted 3,4-ethylenedioxythiophene, a substituted or unsubstituted one condensed thienothiophene, a substituted or unsubstituted oligothiophene, a substituted or unsubstituted ths (oligoarylenyl) amine, an optionally substituted spiro compound or an optionally substituted benzidine compound.
  • the charge-transporting group may also be a substituted or unsubstituted oxadiazole, a substituted or unsubstituted thiadiazole, a substituted or unsubstituted triazole, a substituted or unsubstituted pyridine, fluoroaryl, a fluoroheteroaryl, a substituted or unsubstituted benzimidazole, a substituted or unsubstituted perylene or perylene Derivative, a substituted or unsubstituted tris (phenylquinoxaline), a substituted or unsubstituted silanol compound, or an optionally substituted boron-containing compound.
  • M 1 and M 2 may each independently be a metal selected from the group consisting of Cu, Ag, Au, Pd, Pt, Rh, Ir, Re, Os, Mo, W and Zn.
  • M 1 and M 2 are each independently of one another a metal selected from the group consisting of Cu, Ag and Au.
  • At least one of the metals M 1 or M 2 is Cu or Ag.
  • both metals M 1 and M 2 are each independently of one another Cu or Ag.
  • both metals M 1 and M 2 are each Cu.
  • the bridging ligands L 1 and L 2 can, as set out above, selected from the group consisting of I, Br, Cl, CN, OCN, SCN, N 3 , and alkyne radicals having up to 10 carbon atoms and thioalkyl radicals with bis to be 10 carbon atoms.
  • At least one of the bridging ligands L 1 or L 2 is selected from the group consisting of I, Cl, Br, CN and SCN. According to a more preferred embodiment, both bridging ligands L 1 and L 2 are each selected from the group consisting of I, Cl, Br, CN and SCN.
  • both bridging ligands L 1 and L 2 are the same, especially selected from the group consisting of I, Cl, Br, CN and SCN.
  • both bridging ligands L 1 and L 2 are each I.
  • the metal complex compound MK has a structure of the formula (II):
  • R 1 , R 2 , R 3 , R 4 and R 5 , M 1 , M 2 , L 1 and L 2 are as defined above.
  • the metal complex compound MK has a structure selected from the group consisting of the formulas (III) to (IX):
  • R 1 , R 2 , R 3 , R 4 , M 1 , M 2 , L 1 and L 2 are as defined above.
  • the radicals R 1 and R 2 are each unsubstituted or substituted phenyl radicals
  • R 3 and R 4 are each alkyl radicals having up to five carbon atoms
  • M 1 and M 2 are each Cu or Ag and L 1 and L 2 each I, Br or Cl.
  • radicals R 1 and R 2 may each be unsubstituted or substituted phenyl radicals, R 3 and R 4 together with N is a heterocycloalkyl radical having up to five carbon atoms (eg, -NC 5 H 10, -NC H 8 ) M 1 and M 2 each Cu or Ag and L 1 and L 2 are each I, Br or Cl.
  • radicals are very particularly preferably each defined as follows:
  • M 1 and M 2 are most preferably both Cu
  • L 1 and L 2 are most preferably both I.
  • R 3 and R 4 are very particularly preferably both methyl radicals, and / or
  • R 1 and R 2 are most preferably both phenyl radicals.
  • Metal Complex Compound MK has a structure of the formula (X) on:
  • R 5 is as defined in claim 1 or 4.
  • the metal complex compound MK has a structure of one of the formulas (XI) to (XIII):
  • the metal complex compound MK can have any optical properties and energy states.
  • the energy gap ⁇ between the lowest triplet state T1 and the overlying singlet state S1 is between 50 cm -1 and 3000 cm -1 , preferably between 500 cm -1 and 2000 cm -1 .
  • An inventive metal complex compound MK can be used as an optically active compound, therefore, depending on the conditions and the environment as an emitter compound and / or as an absorber compound. Therefore, a metal complex compound MK of the present invention can also be used as an optically active material in an optically active layer S (hence, a light-emitting or light-absorbing layer). Then, the metal complex compound MK according to the invention is introduced into the optically active layer S or the optically active layer S even consists of the metal complex compound MK according to the invention.
  • the optically active layer S can in turn be part of an optoelectronic device.
  • an optically active layer S comprising a metal complex compound MK according to the present invention.
  • An optically active layer S in the context of the present invention is to be understood in the broadest sense as any layer which is able to emit light under certain conditions in an opto-electronic device (usually under current flow) and / or under certain conditions an opto-electronic device to absorb light and convert it into electrical energy (charge separation or current flow).
  • a layer in the sense of the present invention is to be understood in the widest sense as a (largely) planar geometry.
  • the optically active layer S is preferably not thicker than 1 mm, more preferably not thicker than 0.1 mm, more preferably not thicker than 10 ⁇ , even more preferably not thicker than 1 ⁇ , in particular not thicker than 0.1 ⁇ .
  • the proportion of MetaN complex compound MK at the optically active layer S can be arbitrary.
  • the optically active layer S preferably represents:
  • optically active layer S may optionally additionally contain one or more further components selected from the group consisting of solvents, host molecules W and dyes F.
  • a solvent may in this case be any solvent in which the metal complex compound MK is soluble, preferably readily soluble.
  • the solvent is a non-halogenated solvent.
  • the solvent is a coordinating solvent.
  • Such a coordinating solvent may, for example, be selected from the group consisting of benzene, toluene, tetrahydrothiophene, benzonitrile, pyridine, acetonitrile, trihydrofuran and triarylamine.
  • a solvent in this context may be selected from benzene, toluene, acetonitrile, and mixtures thereof.
  • Host molecules W are to be understood in the broadest sense as any molecules in which the metal complex compound MK can be embedded in the optically active layer S.
  • a host molecule W may have a polymeric structure.
  • a host molecule W may perform other tasks, such as spatial separation between the emitter compound E and dyes F to avoid undesired (quenching) quenching and triplet triplet annihilation under emission abatement, and possibly enhanced carrier injection, improved charge transport and an increased probability of recombination directly on the Emitter connections E allow.
  • the metal complex compound MK is not covalently linked to the host molecules W.
  • the host molecules W do not interfere with the optical properties of the metal complex compound MK (emission / absorption).
  • the host molecules W could be polymers. Such host molecules W are well known in the art.
  • the optically active layer S may optionally additionally contain a dye F.
  • the dye F is preferably itself no metal complex compound MK in the context of the present invention and preferably does not emit light itself during current flow. However, the dye F can optionally change the color of the light emitted by a metal complex compound MK according to the invention. Any desired dye F or else a dye combination can be used here.
  • the dye F can also be a fluorescent and / or phosphorescent dye F, which can shift the emission and / or absorption spectrum of the optically active layer S.
  • diphoton effects can also be used, therefore absorbing two photons with half the energy of the absorption maximum.
  • a fluorescent and / or phosphorescent dye F usually a bathochromic effect is achieved (for example by heat loss). However, a hypsochromic effect can also be achieved (for example by diphoton effects).
  • the dye F may also be a fluorescent polymer (e.g., Superyellow® (SY)), a photoluminescent nanoparticle (such as of silicon), a quantum dot, or an exciplex.
  • the optically active layer S may additionally contain an ionic liquid or a combination of two or more ionic liquids, depending on which optoelectronic device it is used in.
  • an ionic liquid or combination of two or more ionic liquids may be selected from the group consisting of:
  • Methylimidazolium hexafluorophosphates eg, 1-alkyl-3-methylimidazolium hexafluorophosphates, such as 1-methyl-3-methyl- imidazolium hexafluorophosphate, 1-ethyl-3-methyl-imidazolium hexafluorophosphate, 1-propyl-3-methyl-innidazolinohexafluorophosphate, 1-butyl-3-methylimidazolium hexafluorophosphate, 1-benzyl-3-methylimidazolinium hexafluorophosphate), dimethyl innidazolinohexafluorophosphates (eg 1 - Alkyl-2,3-dimethyl-imidazolium hexafluorophosphates such as 1-butyl-2,3-dimethyl-imidazolinohexa-fluorophosphate), 3-methyl-imidazolinohex
  • phosphoniunnbronnid 1-butyl-3-methylpyridinium bis (trifluoromethylsulfonyl) imide, 1-butyl-4-methylpyridinium hexafluorophosphate, 1-butyl-4-methylpyridinium tetrafluoroborate, sodium tetraphenylborate, tetrabutylammonium tetraphenylborate, sodium tetrakis (1-imidazolyl) borate and
  • the optically active layer S may optionally contain one or more electrolytes, such as KCF3SO3.
  • the optically active layer S represents an emitter layer consisting of the metal complex compound MK according to the present invention. As described above, such an optically active layer S is usually incorporated in an opto-electronic device to generate light.
  • another aspect of the invention relates to an opto-electronic device comprising at least one metal complex compound MK according to the present invention and / or at least one optically active layer S according to the present invention.
  • an optoelectronic device is preferably an organochemical optoelectronic device, in which the optically active layer S consists at least predominantly of organic materials, ie of hydrocarbon compounds, the hydrocarbon compounds containing heteroatoms such as nitrogen, phosphorus, oxygen and / or halogens may be substituted.
  • the proportion of metal complex compound MK in the optically active layer S may be 0.1 to 100%. Accordingly, the optically active layer S can consist entirely or largely of the metal complex compound MK or the metal complex compound MK can be present only as a small or large proportion in addition to other compounds (such as, for example, one or more host molecules W). contain.
  • the proportion of metal complex compound MK in the optically active layer S is preferably more than 30 wt%, more than 40 wt%, more than 50 wt .-%, more than 60 wt .-%, more than 70 wt .-%, more than 80 wt .-% or more than 90 wt .-%.
  • the opto-electronic device may be opaque, semi-transparent or (substantially) transparent.
  • the optoelectronic device can be any optoelectronic device which includes a metal complex compound MK according to the invention and / or an optically active layer S according to the invention.
  • the opto-electronic device is an organic light emitting diode (OLED), a light emitting electrochemical cell (LEC), an organic solar cell (Engl. organic solar cell ", OSC), an optical sensor, an organic field effect transistor or an organic laser.
  • OLED organic light emitting diode
  • LOC light emitting electrochemical cell
  • OSC organic solar cell
  • optical sensor an organic field effect transistor or an organic laser.
  • the opto-electronic device may be configured as a thin layer which is not thicker than 5 mm, 2.5 mm, 2 mm, 1, 5 mm, 1 mm, 100 ⁇ m or 10 ⁇ m in total.
  • the layer may also have a thickness in the range of 8-9 ⁇ m, 7-8 ⁇ m, 6-7 ⁇ m, 5-6 ⁇ m, 4-5 ⁇ m, 3-4 ⁇ m, 2-3 ⁇ m, 1-2 ⁇ m or less have 1 ⁇ .
  • OLEDs are known to be composed of several layers. Usually, an anode layer A is on a substrate.
  • the substrate may be made of any material or combination of materials. Glass plates are most commonly used. Alternatively, however, thin metal foils (for example copper, gold, silver or aluminum foils) may also be used. or plastics are used, which allows a higher flexibility of the OLED.
  • anode layer A transparent materials are often used as anode materials. Since at least one of the electrodes must be transparent in order to be able to decouple the light generated in the OLED, either the anode layer A or the cathode layer C must be largely, preferably (almost) completely transparent to the light to be coupled out.
  • Anode layer A usually consists to a large part or (almost) completely of one or more (largely) transparent conductive oxides ("transparent conductive oxides", TCOs)
  • transparent conductive oxides TCOs
  • Such an anode layer A can be, for example, indium tin oxide, aluminum zinc Oxide, fluorine-tin oxide, indium-zinc oxide, PbO, SnO, zirconium oxide, molybdenum oxide, vanadium oxide, tungsten oxide, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene.
  • the anode layer A may also consist of one or more of the abovementioned materials, the anode preferably being composed of indium tin oxide (ITO) (usually (lnOs) o, 9 (SnO 2) o, i).
  • ITO indium tin oxide
  • the roughness of the transparent, conductive oxides used in the anode layer A can be compensated for by the use of an additional hole injection layer (HIL)
  • the hole injection layer can facilitate the injection of positive quasi charge carriers by preventing the transfer of the carrier from the transparent, Poly-3,4-ethylenedioxythiophene (PEDOT), polystyrene sulfonate (PSS), MoO 2 , V 2 O 5 or Cul, especially a mixture of PEDOT and PSS, can be used in the hole injection layer can also prevent the diffusion of metals from the anode layer A into the transition in the hole-line layer 16.
  • a hole transport layer typically a hole transport layer (HTL) is arranged on the anode layer A or hole-injection layer.
  • HTL hole transport layer
  • any hole conductor can be used.
  • electron-rich heteroaromatics such as triarylamines or carbazoles can be used as hole conductors.
  • the hole line layer can fulfill a leveling function and the Energy barrier to the optically active layer S (here: emitter layer, Engl, "layer”, EML, or "light emitting layer", LEL) bridge.
  • the hole-conducting layer can also be referred to as an electron blocking layer (EBL)
  • EBL electron blocking layer
  • the hole conductors preferably have high triplet energies, for example the hole-conducting layer can be a star-shaped heterocycle as tris (4-carbazoyl-9-ylphenyl). amine (TCTA).
  • the optically active layer S which contains at least one complex metal compound MK in connection with the present invention, is applied to the hole-conducting layer.
  • the optically active layer S also consist of this metal complex compound MK.
  • the composition of an optically active layer S will be described in detail above.
  • an electron transport layer can be applied to the optically active layer S.
  • Any electron conductor can be used here, for example electron-deficient compounds such as benzimidazoles, pyridines, triazoles, oxadiazoles (for example 1, 3 , 4-oxadiazole), phosphine oxides and sulfones are used.
  • the electron conduction layer may contain as electron conductor a star-shaped heterocycle such as 1, 3,5-tri (1-phenyl-1H-benzo [d] imidazol-2-yl) phenyl (TPBi).
  • the electron transport layer can serve for energetic leveling between cathode layer C and optically active layer S and on the other hand block holes.
  • a cathode layer C is typically applied to the electron conduction layer. This can for example consist of a metal or a metal alloy. This may comprise, for example, Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more of these metals.
  • the cathode layer C may consist of (largely) optically nontransparent metals, such as Mg, Ca or Al.
  • the cathode layer C may also contain graphite and / or carbon nanotubes (CNTs)
  • the anode layer A should be as transparent as possible, and the cathode layer C may also consist (largely) of semitransparent materials as For example, nanoscale silver wires exist.
  • the cathode layer can be vapor-deposited, for example, in a high vacuum.
  • a thin protective layer may optionally be applied between the cathode layer C and the ETL.
  • This may for example contain lithium fluoride, cesium fluoride and / or silver and may optionally be applied by vapor deposition.
  • OLEDs can also be produced, for example, as illuminated foils, as luminous labels in smart packaging or as innovative design elements, and can also be used in cell recognition and analysis.
  • An OLED preferably comprises at least the following layers:
  • anode layer A preferably comprising indium tin oxide, indium zinc oxide, PbO, SnO, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene;
  • a cathode layer C preferably comprising Al, Ca, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more of these metals,
  • an OLED comprises at least the following layers:
  • an anode layer A in particular one comprising indium tin oxide
  • HTL a hole line layer
  • ETL an electron conduction layer
  • a cathode layer C preferably comprising Al, Ca or Mg,
  • the layers either directly adjoin or still one or more layer (s) may be therebetween.
  • the electrons (hence negative charge carriers) migrate in operation from the cathode towards the anode, which provides the holes (hence positive quasi charge carriers). Holes and electrons meet in the ideal case in the optically active layer S, which is why this can also be referred to as a recombination layer. Clashing electrons and holes form a bound state (exciton). From an exciton, a metal complex compound MK can be excited by energy transfer. This metal complex compound MK can relax into the ground state and thereby emit a photon.
  • the color of the emitted light depends on the energy gap ⁇ between the excited and the ground state and can by variation of the metal complex compound MK (about one of the radicals R 1 -R 5 , M 1 , M 2 , L 1 and / or L 2 in the metal complex compound MK according to formula (I)) can be selectively varied.
  • the optoelectronic device according to the invention is an organic solar cell (OSC)
  • OSC organic solar cell
  • the device comprises the metal complex compound MK as part of an absorber layer.
  • the proportion of metal complex compound MK in the absorber layer is preferably between 30 and 100% by weight.
  • two electrodes are also provided for OSCs. Between these, the absorber layer is arranged, in which the metal complex compound MK described in the present application is used.
  • the metal complex compound MK described above can emit light.
  • the radicals R 1 -R 5 , M 1 , M 2 , L 1 and / or L 2 in the metal complex compound MK can thereby the ⁇ -distance between the first excited triplet state T1 and the singlet ground state SO and the first excited singlet state S1 and the singlet ground state SO, so that it is possible to vary the wavelength of the emitted light.
  • Cu (I) complexes excellent results were achieved in this regard.
  • a single-layer OSC can have the following layers: A) a first electrode layer to a large extent or (almost) completely consisting of one or more (largely) transparent conductive oxides ("transparent conductive oxides", TCOs), for example indium tin oxide, aluminum zinc oxide, Fluorine-tin-oxide, indium-zinc-oxide, PbO, SnO, graphite, doped Si, doped Ge, doped GaAs, doped polyaniline, doped polypyrrole and / or doped polythiophene, in particular indium tin oxide (ITO) (eg In0 3 ) o, 9 (Sn0 2 ) o, i);
  • ITO indium tin oxide
  • an absorber layer S (corresponding to the optically active layer S in OLEDs) containing at least one metal complex compound MK; and C) A second electrode layer of a metal or a metal alloy, such as Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more of these metals , Carbon nanotubes, CNTs) and / or nanoscale silver wires, in particular Mg, Ca or Al,
  • a metal or a metal alloy such as Al, Au, Ag, Pt, Cu, Zn, Ni, Fe, Pb, In, W, Pd and / or mixtures or alloys of two or more of these metals , Carbon nanotubes, CNTs) and / or nanoscale silver wires, in particular Mg, Ca or Al,
  • the single-layer OSC is typically applied to one substrate (such as the first electrode layer) and protected on the other outside with a protective layer.
  • An organic solar cell may also be referred to as an organochemical photovoltaic device (OPV).
  • OLED organochemical photovoltaic device
  • An optical sensor may, for example, be an optical sensor which measures the light intensity. Also, the optical sensor may optionally determine the light intensity of light of a particular wavelength range. An optical sensor may also be part of an array of optical sensors (hence an array), as used, for example, as an image sensor in a digital camera.
  • An opto-electronic device can be manufactured by any method.
  • the optically active layer S applied wet-chemically applied to the corresponding component of the opto-electronic device. This can be done for example by a printing process, spin coating, dropcasting, slot casting, curtain casting or a rolling process.
  • One aspect of the present invention relates to a method for producing an opto-electronic device according to the present invention, wherein at least one metal complex compound MK according to the present invention is printed on a substrate.
  • the printing can take place, for example, by means of a printing process (for example inkjet printing, intaglio printing or doctoring), in which case the composition comprising the metal complex compound MK can optionally be mixed with agents for improving the flow properties
  • a printing process for example inkjet printing, intaglio printing or doctoring
  • agents for improving the flow properties for example, such an agent may be selected from the group consisting of polyethyloxides (polyethylene glycols), polyethylenediamines, polyacrylates (eg
  • Polymethyl methacrylate PMMA
  • polyacrylic acid and its salts superabsorbents
  • substituted or unsubstituted polystyrenes e.g., polyhydroxystyrene
  • polyvinyl alcohols polyesters or polyurethanes
  • polyvinylcarbazoles polytriarylamines
  • polythiophenes polythiophenes
  • polyvinylidene-phenylenes Combinations of two or more agents may also be used.
  • an opto-electronic device according to the invention can also be used to emit light.
  • the present invention comprises a method for producing light of a specific wavelength, comprising the following steps:
  • the present invention also includes a method of producing blue, green, yellow, orange or red emission.
  • light in the range of 400-800 nm may be emitted, such as in the range of 400-500 nm, 450-550 nm, 500-600 nm, 550-650 nm, 600-700 nm, 650 -750 nm and / or 700-800 nm.
  • the light generated in this case has an emission maximum in the range of 420 to 600 nm.
  • the light generated thereby has an emission maximum in the range of 420 to 550 nm, even more preferably 420 to 500 nm.
  • the optoelectronic device according to the present invention is an OLED, it can also be used, for example, as a large-area light source, as a luminous wallpaper, a luminous window, a luminescent label, a luminescent poster or a flexible screen.
  • the opto-electronic device according to the present invention is an OSC, it can also be used, for example, as a roll-up solar cell (for mobile applications such as smartphones, laptops, tablets, etc.), as an architectural element (eg wall or roof cladding element) or as Component in the traffic engineering area (eg in the automotive, aircraft, train, and / or ship area) are used. It will be understood that such products containing the optoelectronic device according to the invention are also subject matter of the present invention.
  • the metal complex compound MK of the invention is composed of two organic ligands OL, two bridging ligands L 1 and L 2 and two metals M 1 and M 2 .
  • another aspect of the present invention comprises an organic ligand OL of the structure of formula (XIV):
  • C 1 , C 2 , F 1 , R 1 , R 2 , R 3 , R 4 and R 5 are as defined in connection with the metal complex compound MK.
  • This organic ligand OL can be used to prepare a metal complex compound MK according to the invention.
  • the method of producing MK starting from OL is also the subject of the invention.
  • another aspect of the present invention comprises the use of an organic ligand OL according to the present invention for preparing a metal complex compound MK comprising the step of contacting the organic ligand OL with one or more metal salts containing M 1 and M 2 as cations and L 1 and L 2 as anions.
  • Another aspect of the present invention relates to a metal complex compound MK having a structure of the formula (I):
  • carbon atoms C 1 and C 2 are part of a mononuclear aromatic or heteroaromatic ring system F 1 having a total of up to 6 carbon atoms, the ring system F 1 being substituted by R 5 ;
  • N represents a nitrogen atom
  • P represents a phosphorus atom
  • R 1 and R 2 are each an atom or a radical independently selected from the group consisting of -R a , -OR a , -SR a , -C (O) -R a , -C (O) -OR a , - OC (O) -R a , -NH-R a , -NR a R b , -R a -NC (O) -R b , -Si (R a ) x (OR b ) 3 -x, hydrogen and halogen wherein R a and R b are each an aryl, heteroaryl, alkyl, cycloalkyl, alkenyl, cycloalkenyl, alkynyl, cycloalkynyl, alkylcycloalkyl, heteroalkyl, heterocycloalkyl, heteroalkenyl, heterocycloalkenyl, heteroalkynyl , Cycloalky
  • Heteroalkylcycloalkyl, Heteroalkylcycloalkenyl-, Heteroalkylcycloalkinyl-, Heteroalkenylcycloalkenyl-, Heteroalkenylcycloalkinyl-, Heteroalkinylcycloalkenyl-, Heteroalkinylcycloalkinyl-, aralkyl or heteroaralkyl radical having up to 40 carbon atoms and may each be unsubstituted or substituted, wherein x 1, 2 or 3 ; R 3 and R 4 together with the nitrogen atom to which they are attached form a 6 or 7 atom aliphatic ring system which may optionally be unsubstituted or substituted;
  • R 5 is selected from the group consisting of hydrogen, -R c -NR d R e , halo, -R f , -NR g R h , -R c -NR g R h , -R c -OR g , -R c -SR g , -R c -C (O) -R g , -R c -C (O) -R g , -R c -OC (O) -R g , -C (O) -OR g , -R c -SiR d R e R g , -R c -SiR g , -R c -SO 2 -R g , -R c -PO 4 R d R e R g , R c -PO 4 R d R e R g , R c -PO 4 R d R
  • R c is an unbranched or branched alkylene radical, an unbranched or branched heteroalkylene radical, an unbranched or branched alkenylene radical, is an unbranched or branched heteroalkenylene radical, an unbranched or branched alkynylene radical or an unbranched or branched heteroalkynylene radical each having up to 40 carbon atoms and may each be unsubstituted or substituted or R c is a covalent bond,
  • R d and R e are connected unbranched or branched alkylene, alkenylene, alkynylene, heteroalkylene, heteroalkenylene, or heteroalkynylene radicals which, together with the radical to which they are attached, are a heterocycloalkyl, heteroaryl, heterocycloalkenyl form - or heterocycloalkinyl radical having up to 10 carbon atoms and may each be unsubstituted or substituted, wherein R f is a branched or unbranched alkyl radical, an alkyl heterocycloalkyl radical, a heterocycloalkyl radical, a cycloalkyl radical, an unbranched or branched alkenyl radical, a cycloalkenyl radical, an unbranched or branched alkynyl radical, a cycloalkynyl radical, an aryl radical, an alkylcycloalkyl radical, an unbranched or branched heteroalkyl radical,
  • the metal complex compound MK of the present invention may thus also have a structure of the following formula (XVI):
  • radicals R 1 , R 2 , R 5 , F 1 , M 1 , M 2 , L 1 and L 2 can be defined as above,
  • R 5 but optionally also H can be, and
  • F 3 is a 6 or 7 atom aliphatic ring system which may optionally be unsubstituted or substituted.
  • F 3 is an unsubstituted aliphatic ring system comprising the N and 5 carbon atoms to form a piperidinyl moiety.
  • the present invention also includes an organic ligand OL of the structure of the formula (XIV): (XIV) where the radicals R 1 , R 2 , R 5 , F 1 , M 1 , M 2 , L 1 and L 2 can be defined as above,
  • R 5 but optionally also H can be, and
  • the organic ligand OL of the present invention may thus also have a structure of the following formula (XVII):
  • radicals R 1 , R 2 , R 5 , F 1 , M 1 , M 2 , L 1 and L 2 can be defined as above,
  • R 5 but optionally also H can be, and
  • F 3 is a 6 or 7 atom aliphatic ring system which may optionally be unsubstituted or substituted.
  • F 3 is an unsubstituted aliphatic ring system containing the N and 5
  • radicals R 1 , R 2 , F 1 , M 1 , M 2 , L 1 and L 2 can be defined as above.
  • radicals R 1 , R 2 , R 5 , F 1 , M 1 , M 2 , L 1 and L 2 are preferably defined as in the above preferred embodiments.
  • the aliphatic ring system formed by R 3 and R 4 together with the nitrogen atom to which they are attached most preferably comprises 5 carbon atoms, so that N, R 3 and R 4 most preferably form a piperidinyl ring.
  • the aliphatic ring system formed by R 3 and R 4 together with the nitrogen atom to which they are attached may be an unsubstituted cycloalkyl, cycloalkenyl or cycloalkynyl radical or may optionally be mono- or polysubstituted, for example with a halogen, an alkyl, alkenyl, alkynyl, heteroalkyl, heteroalkenyl and / or heteroalkynyl radical and / or a functional group.
  • the aliphatic ring system formed by R 3 and R 4 together with the nitrogen atom to which they are attached is not further substituted and together with the nitrogen represents a piperidinyl radical.
  • C 1 , C 2 , F 1 , R 1 , R 2 , R 5 , M 1 , M 2 , L 1 and L 2 may also be defined as in the preferred embodiments described above.
  • this meta-complex compound MK can be used as described above in an optically active layer S and an opto-electronic device, for example, to generate light.
  • the unsubstituted organic ligand 2.1 corresponds to the compound shown in WO 2013/014066.
  • the corresponding organic ligand OL was stirred for several hours with an excess of a corresponding metal halide compound in toluene.
  • the metal complex compounds MK was then isolated after filtration by crystallization in the cold.
  • the metal halide compound Cul (copper iodide) or CuBr (copper bromide) was used in the examples shown.
  • the metal complex compounds MK had the following properties, which are shown in Table I:

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Abstract

L'invention concerne des composés complexes métalliques MK qui ont une structure de la formule (I) dans laquelle les atomes de carbone C1 et C2 sont une partie d'un système cyclique mononucléaire aromatique ou hétéroaromatique F1 comportant au total jusqu'à 6 atomes de carbone. L'invention est caractérisée en ce que le système cyclique F1 est substitué par R5, R5 étant l'hydrogène. La présente invention concerne en outre une couche optiquement active S et un dispositif optoélectronique, qui contient un composé complexe métallique de l'invention, et un procédé de fabrication d'un tel dispositif optoélectronique et de génération de lumière au moyen de celui-ci. En outre, l'invention concerne un ligand organique OL de la formule (XIV) qui est nécessaire pour la production du composé complexe métallique.
PCT/EP2015/069891 2014-09-02 2015-09-01 Composé complexe métallique à solubilité amélioré WO2016037888A1 (fr)

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Citations (2)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
WO2013014066A1 (fr) * 2011-07-26 2013-01-31 Eberhard Karls Universität Tübingen Composés de type complexes dotés d'un ligand pourvu d'un donneur n et d'un donneur p, et leur utilisation dans le domaine électro-optique
WO2014184316A1 (fr) * 2013-05-16 2014-11-20 Cynora Gmbh Complexes de cuivre (i) et d'argent (i) comme matériaux luminescents dans des lampes à faible consommation d'énergie et des lampes fluorescentes

Patent Citations (2)

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Publication number Priority date Publication date Assignee Title
WO2013014066A1 (fr) * 2011-07-26 2013-01-31 Eberhard Karls Universität Tübingen Composés de type complexes dotés d'un ligand pourvu d'un donneur n et d'un donneur p, et leur utilisation dans le domaine électro-optique
WO2014184316A1 (fr) * 2013-05-16 2014-11-20 Cynora Gmbh Complexes de cuivre (i) et d'argent (i) comme matériaux luminescents dans des lampes à faible consommation d'énergie et des lampes fluorescentes

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LIANG L-C ET AL: "CATALYTIC SUZUKI COUPLING REACTIONS BY AMIDO PHOSPHINE COMPLEXES OF PALLADIUM", ORGANOMETALLICS, ACS, WASHINGTON, DC, US, vol. 24, no. 3, 23 December 2004 (2004-12-23), pages 353 - 357, XP001236760, ISSN: 0276-7333, DOI: 10.1021/OM0492395 *
MARKUS J. LEITL ET AL: "Brightly Blue and Green Emitting Cu(I) Dimers for Singlet Harvesting in OLEDs", JOURNAL OF PHYSICAL CHEMISTRY. A, MOLECULES, SPECTROSCOPY,KINETICS, ENVIRONMENT AND GENERAL THEORY, vol. 117, no. 46, 22 August 2013 (2013-08-22), US, pages 11823 - 11836, XP055229007, ISSN: 1089-5639, DOI: 10.1021/jp402975d *
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