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WO2017216299A1 - Molécule émettrice à base d'accepteurs à double fluorescence de type benzène-(poly)carboxylate - Google Patents

Molécule émettrice à base d'accepteurs à double fluorescence de type benzène-(poly)carboxylate Download PDF

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WO2017216299A1
WO2017216299A1 PCT/EP2017/064689 EP2017064689W WO2017216299A1 WO 2017216299 A1 WO2017216299 A1 WO 2017216299A1 EP 2017064689 W EP2017064689 W EP 2017064689W WO 2017216299 A1 WO2017216299 A1 WO 2017216299A1
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formula
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Inventor
Paul Kleine
Ramunas Lygaitis
Reinhard Scholz
Simone Lenk
Sebastian Reineke
Jouzas Vidas GRAZULEVIUS
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Technische Universitaet Dresden
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Technische Universitaet Dresden
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D209/00—Heterocyclic compounds containing five-membered rings, condensed with other rings, with one nitrogen atom as the only ring hetero atom
    • C07D209/56—Ring systems containing three or more rings
    • C07D209/80—[b, c]- or [b, d]-condensed
    • C07D209/82—Carbazoles; Hydrogenated carbazoles
    • C07D209/86—Carbazoles; Hydrogenated carbazoles with only hydrogen atoms, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07C—ACYCLIC OR CARBOCYCLIC COMPOUNDS
    • C07C229/00—Compounds containing amino and carboxyl groups bound to the same carbon skeleton
    • C07C229/52—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton
    • C07C229/54—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring
    • C07C229/56—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position
    • C07C229/58—Compounds containing amino and carboxyl groups bound to the same carbon skeleton having amino and carboxyl groups bound to carbon atoms of six-membered aromatic rings of the same carbon skeleton with amino and carboxyl groups bound to carbon atoms of the same non-condensed six-membered aromatic ring with amino and carboxyl groups bound in ortho-position having the nitrogen atom of at least one of the amino groups further bound to a carbon atom of a six-membered aromatic ring, e.g. N-phenyl-anthranilic acids
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D219/00—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems
    • C07D219/02—Heterocyclic compounds containing acridine or hydrogenated acridine ring systems with only hydrogen, hydrocarbon or substituted hydrocarbon radicals, directly attached to carbon atoms of the ring system
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D223/00—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom
    • C07D223/14—Heterocyclic compounds containing seven-membered rings having one nitrogen atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
    • C07D223/18—Dibenzazepines; Hydrogenated dibenzazepines
    • C07D223/22—Dibenz [b, f] azepines; Hydrogenated dibenz [b, f] azepines
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D265/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one oxygen atom as the only ring hetero atoms
    • C07D265/28—1,4-Oxazines; Hydrogenated 1,4-oxazines
    • C07D265/34—1,4-Oxazines; Hydrogenated 1,4-oxazines condensed with carbocyclic rings
    • C07D265/38—[b, e]-condensed with two six-membered rings
    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D279/00—Heterocyclic compounds containing six-membered rings having one nitrogen atom and one sulfur atom as the only ring hetero atoms
    • C07D279/10—1,4-Thiazines; Hydrogenated 1,4-thiazines
    • C07D279/14—1,4-Thiazines; Hydrogenated 1,4-thiazines condensed with carbocyclic rings or ring systems
    • C07D279/18—[b, e]-condensed with two six-membered rings
    • C07D279/22—[b, e]-condensed with two six-membered rings with carbon atoms directly attached to the ring nitrogen atom

Definitions

  • the present invention relates to compounds as described herein, as well as their use as emitter or carrier material in an optoelectronic component.
  • optoelectronic component includes organic integrated circuits (OICs), organic field effect transistors (OFETs), organic thin film transistors (OTFTs), organic light emitting transistors (OLETs), organic solar cells (OSCs), organic optical Detectors, organic photoreceptors, organic field quench devices (OFQDs), organic light-emitting electrochemical cells (OLECs), organic laser diodes (O-lasers) and organic electroluminescent devices such as organic light-emitting diodes (OLEDs) understood.
  • OICs organic integrated circuits
  • OFETs organic field effect transistors
  • OFTs organic thin film transistors
  • OLETs organic light emitting transistors
  • OSCs organic solar cells
  • OFQDs organic field quench devices
  • OFQDs organic light-emitting electrochemical cells
  • O-lasers organic laser diodes
  • organic electroluminescent devices such as organic light-emitting diodes (OLEDs) understood.
  • OLEDs organic electroluminescent devices
  • the first generation of OLEDs was based exclusively on fluorescent emitter molecules that emit light from the excited singlet state Si and were therefore restricted to a quantum yield of 25% according to the spin statistics.
  • triplet states via phosphorescence were used for the light emission by targeted introduction of heavy atoms (heavy atom effect) and a resulting increase in spin-orbit coupling. It comes from a stimulated triplet state Ti, by reversing the spin to the transition to the ground state So. By a more long-lasting radiation process by this phosphorescent As a result, the internal quantum efficiency increases up to 100%.
  • iridium or other noble metal-containing molecular compounds which according to the prior art frequently carbazo derivatives, for example bis (carbazolyl) biphenyl, ketones continue (WO 2004/093207), phosphine oxides, sulfones (WO 2005/003253), triazine compounds such as Triazinyispirobifluoren (WO 2005 No. 053055 and WO 2010/05306) are used as phosphorescent emitters.
  • metal complexes such as bis (2-methyl-8-quinolinolato-N1, 08) - (1, 1 'biphenyl-4-olato) aluminum (BAIq) or bis [2- (2-benzothiazole) phenolatj zinc (II) used.
  • the present invention is classified in the third generation of emitter molecules.
  • Pure organic compounds which have a small internal energy barrier between Singuiett and triplet excitation, can thermally excite triplet excitons under spin reversal to radiant singlet states.
  • Light-emitting organic compounds that follow this principle of the thermally activated "spin-flip" from non-radiative triplet to radiating singlet state are referred to as TADF emitters (thermally activated delayed fluorescence), from this third generation of organic emitter molecules It expects to provide long-lived blue emitters with improved efficiency even under increased current density, since TADF emitters represent purely organic compounds and their characteristics are largely determined by the geometry and choice of donor (D) and acceptor (A) groups a large field of possible molecular structures.
  • the compounds described herein are characterized by a small energetic splitting between the lowest excited triplet and the lowest excited singlet, and in such materials, a thermally activated delayed fluorescence mechanism can exploit a backward triplet to singlet system transition to triplet states by thermal excitation in singlets to convict. These singlet states then contribute to radiative recombination, which increases the internal quantum efficiency beyond 25%.
  • the donor (D) acceptor (A) structures described herein, in which benzene derivatives (benzene (poly) caboxylates, ketones, sulfones, phosphorous oxides, and benzonitriles) function as acceptor moieties, are particularly aimed at not exclusively, for stable and long-lasting emission in the blue spectral emission range.
  • the present invention is directed to a compound comprising at least one donor group and at least one acceptor group of general structural formula (I)
  • R x with each occurrence is independently selected from the group consisting of hydrogen
  • n is selected from 0, 1, 2, 3, 4 or 5;
  • n is selected from 0, 1, 2, 3, 4, 5 and 6;
  • R x is selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.
  • the present invention is directed to the use of a compound as described herein in an opto-electronic device, such as an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field effect transistor (O-IC). FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, an organic photoreceptor, an organic field quench device (O-LET).
  • OLED organic electroluminescent device
  • O-IC organic integrated circuit
  • O-IC organic field effect transistor
  • FET organic thin film transistor
  • O-LET organic light emitting transistor
  • O-SC organic solar cell
  • O-SC organic solar cell
  • O-LET organic optical detector
  • O-LET organic photoreceptor
  • O-LET organic field quench device
  • FQD light-emitting electrochemical cell
  • O-laser organic laser diode
  • the present invention is also directed to an optoelectronic device containing at least one compound as described herein.
  • At least one as used herein means 1 or more, ie 1, 2, 3, 4, 5, 6, 7, 8, 9 or more.
  • At least one donor group thus means, for example, at least one type of donor - group, ie that is, one kind of donor group or a mixture of several different donor groups may be meant.
  • the present invention relates to metal-free compounds which can be used both as emitter materials, in particular emitter materials emitting in the blue spectral range, in optoelectronic and electronic components.
  • a compound includes at least one donor and at least one acceptor group.
  • acceptor group refers to a chemical group having electron-withdrawing properties.
  • a “donor group” as used herein refers to a chemical group having electron-donating properties.
  • such an electron-donating group may be an aryl or heteroaryl group as defined herein.
  • a steric hinderance between donor and acceptor causes a strong twist about the donor-acceptor bond, so that a nearly perpendicular dihedral angle is established for this bond.
  • This geometry ensures a spatial separation of the charge carrier densities of electrons and holes in the emitter molecules according to the invention.
  • the acceptor group not only effects steric repulsion between donor and acceptor moieties in the emitter molecule, which minimizes ⁇ conjugation between donor and acceptor moieties and is indispensable to the TADF process, but possesses them beyond that intrinsic dual fluorescence.
  • This dual fluorescence can be targeted to the charge-separated CT channel by selecting the donor group as defined herein ( Figure 1). The gain is ensured by an increased transition dipole moment, which results in an increase in emission from the CT channel.
  • the acceptor group is a benzene derivative, in particular a benzene (poly) carboxylate, a benzene ketone, a benzene sulfone, a benzene phosphorus oxide or a benzonitrile.
  • benzene (poly) carboxylates Particularly preferred are benzene (poly) carboxylates.
  • the present invention is directed to a compound comprising at least one donor group and at least one acceptor group of general structural formula (I)
  • the proviso that at least one R x is selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.
  • n is at least 1, preferably 1, 2 or 3. In such embodiments, o may be 0 in particular.
  • Ry with each occurrence is independently selected from the group consisting of R CO 2 R x , COR x , SO 2 R x , and P (O) (R x ) 2 , in particular R 1 C0 2 R x and COR x .
  • R x with each occurrence is independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and NR 2 R 3 .
  • m is at least 1, preferably 1, 2, 3, 4 or 5.
  • R x is preferably a substituted or unsubstituted aryl or substituted or unsubstituted heteroaryl
  • C3-C20 alkyl group refers to a linear or branched carbon group comprising from 3 to 20 carbon atoms, by way of example, without limitation, especially groups which are selected from the group consisting of propyl, isopropyl, c-propylene, n-butyl, sec-butyl, isobutyl and t-butyl groups, the above-mentioned groups each being substituted or unsubstituted, and when substituted, the substituents are preferably selected from the group consisting of halogens and pseudo-halogens (-CN, -N 3, -OCN, -NCO, -CNO, -SCN, -NCS, -SeCN).
  • C3-C20 alkenyl group refers to a linear or branched carbon group comprising 3 to 20 carbon atoms and having at least one carbon-carbon unsaturated bond.
  • groups which are selected from the group consisting of allyl, isobutenyl and isopentenyl, where the abovementioned groups may each be substituted or unsubstituted.
  • the substituents are preferably selected from the group consisting of halogens and pseudohalogens (-CN, -N 3 , - OCN, -NCO, -CNO, -SCN, -NCS, -SeCN).
  • aryl refers to either a monocyclic aromatic group such as phenyl or a fused (annealed, polynuclear) aromatic polycyclic group, for example, naphthalene or phenanthrenyl Significance of, but not limited to, two or more single (mononuclear) aromatic rings fused together, by way of example especially groups selected from the group consisting of phenyl, naphthyl, anthracene, phenanthrenyl, fluorenyl, pyrenyl, dihydropyrenyl, chrysenyl, peryienyl, Fluoranthenyi, Benzanthracenyi, Benzphenanthrenyi, tetracenyl, pentacenyl and benzpyrenyl, wherein the above groups, according to some embodiments, may each be substituted or unsubstituted .
  • the substituents are preferably selected from the group from halogens and pseudohalogens (-CN, -N3, -OCN, -NCO, -CNO, -SCN, -NCS, -SeCN) and linear or branched alkyl or alkenyl groups having up to 20, preferably up to 6 carbon atoms.
  • a "heating aryl” as used herein refers to either a monocyclic aromatic group or a fused (fused, polynuclear) aromatic polycyclic group as defined above containing at least one heteroatom, for example, selected from the non-limiting group consisting of O, S
  • groups are understood which are selected from the group consisting of furanyi, difuranyi, terfuranyl, benzofuranyi, isobenzofuranyl, dibenzofuranyl, thienyl, dithienyl, terthienyi, benzothienyi, isobenzothienyi, benzodithienyl, benzotrithienyl, Pyrrolyl, indolyl, isoindolyl, carbazolyi, pyridinyl, quinolinyl, isoquinolinyl, acridinyl, phenanthridinyl, benzo-5,6-quinolinyl
  • the compound according to formula (I) is a compound of general structural formula II:
  • R with each occurrence is independently selected from the group consisting of -CH 2 -, -CH 2 CH 2 - and a linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl group;
  • R x with each occurrence is independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, CF 3, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and NR 2 R 3 , wherein R 2 and R 3 with each occurrence are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched C 3 -C 20 alkyl or alkenyl, aryl and heteroaryl; m is selected from 0, 1, 2, 3, 4 or 5; n is selected from 0, 1, 2, 3, 4,
  • n + o> 1 and m + n + o 6. More preferably, n + o is 1, 2 or 3. In further preferred embodiments n is 1, 2 or 3 and o is 0.
  • R y with each occurrence is independently selected from the group consisting of R CO 2 R x , COR x , SO 2 R x , and P (O) (R x ) 2 , in particular R C0 2 R x and COR x .
  • R x with each occurrence is independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl, substituted or unsubstituted Aryl, substituted or unsubstituted heteroaryl and NR 2 R 3 .
  • R, R 2 , R 3 , R 4 , R 5 , R 6 , R 7 and R 8 are independently selected from the group consisting of hydrogen, bromine, methyloxy, methyl, ethyl, CF 3, linear or branched C3-C2o alkyl or alkenyl and aryl;
  • R x or R x is attached directly to the central ring of the compound of formula (I) or (II) (ie, not R x in C0 2 R x , R 1 C0 2 R x , COR x , S0 2 R x and P (0) (R x ) 2 ), radicals of the formula (III).
  • at least one R x is a compound of the formula (III), ie m is at least 1 and R x is a radical of the formula (III).
  • X is nothing, ie the two aromatic rings of the compound of formula (III) are linked only through the N atom, but preferably X is a direct bond, S, O, C (CH 3 ) 2, C (CH 2 CH 3 ) 2 or C (R 9 ) 2 .
  • R 19 is preferably methyl, ethyl, linear or branched C 3 -C 20 alkyl or alkenyl or Ce-u aryl, in particular methyl or phenyl.
  • the proviso is that when X is O, none of R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 is hydroxyl.
  • At least one of R, R 12 R 13 R 14 R 15 R 16 R 17 and R 18 is f f -f -butyl.
  • R x , R 2 and R 3 is a group represented by formula (III-1), (III-2), (III-3) , (III-4), (III-5) or (III-6):
  • R x or R x is attached directly to the central ring of the compound of formula (I) or (II) (ie, not R x in C0 2 R x , R CO 2 R x , COR x , SO 2 R x and P (O) (R x ) 2 ), radicals of the formula (III-1) to (III-6), in particular (III-2), (III-3 ), (III-4) or (III-5), most preferably (III-5).
  • At least one R x is a compound of the formula (III), ie m is at least 1 and R x is a radical of the formulas (III-1) to (III -6), in particular (III-2), (III-3), (III-4) or (III-5), most preferably (III-5).
  • the donors of formulas (III) and (III-1) to (III-6) can be used to realize a broad color spectrum while retaining acceptor functionality.
  • those of the formulas (III-2), (III-3) or (III-4) are used.
  • Different of these donors can also be combined if m> 1.
  • the compound of the formula (I) or (II) is a compound represented by formula (IV), (V), (VI), (VII), (VIII), (IX), (X ), (XI), (XII), (XIII), (XIX) or
  • R x , R 2 , R 22 , R 23 , R 24 , R 25 and R 26 are each independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, CF 3, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl and NR 2 R 3 , wherein R 2 and R 3 with each occurrence are independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched C3-C20 alkyl or alkenyl, aryl and heteroaryl.
  • R 2 , R 22 , R 23 , R 24 , R 25 and R 26 are each independently selected from the group consisting of hydrogen, hydroxyl, methyl, ethyl, linear or branched, substituted or unsubstituted C 3 -C 20 alkyl or Alkenyl, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl, and NR 2 R 3 , especially hydrogen, substituted or unsubstituted aryl, substituted or unsubstituted heteroaryl.
  • R x is selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl.
  • R 2 , R 22 , R 23 , R 24 , R 25 and R 26 is selected from substituted or unsubstituted aryl and substituted or unsubstituted heteroaryl. It is preferred that this is in the ortho-position to the / a C02R X, R C0 2 R x, COR x, S0 2 R x, or P (0) (R x). 2
  • R x , R 2 , R 3 , R 21 , R 22 , R 23 , R 24 , R 25 and R 26 represents a group represented by formula (III) as defined herein or a group represented by formula (III-1), (III-2), (III-3), (III-4), (III-5) or (III-6) as defined herein.
  • R 21 , R 22 , R 23 , R 24 , R 25 and R 26 is a group of formula (III), (III-1), (III-2), (III-3), (III -4), (III-5) or (III-6), more preferably (III-2), (III-3), (III-4) or (III-5), most preferably (III-5) , It is preferred that this group is ortho to the C0 2 R x , R C0 2 R x , COR x , S0 2 R x , or P (0) (R x ) 2 .
  • the group of formula (III) in this context is subject to the proviso that when X is O, none of R 11 , R 12 , R 13 , R 14 , R 15 , R 16 , R 17 and R 18 is hydroxyl is.
  • n 1, 2 or 3, preferably 1, and R x in the radical C02R X is methyl, ethyl or C3-20 alkyl, preferably methyl; and
  • R x is a substituted or unsubstituted aryl or heteroaryl, in particular one of the formula (III), (III-2), (III-3), (III-4) or (III-5), particularly preferably (III-2), (III-3), (III-4), (III-5), most preferably (III-5);
  • the radicals according to (2) are preferably in ortho position to the radicals (1). In such embodiments, preferably, there is no R 1 -CN.
  • the compound according to the invention is a compound represented by formula (IV-1), (IV-2), (IV-3), (IV-4), (IV-5) or (IV- 6):
  • the compounds according to the invention are those of the formulas 1.1.1, 1.2.1, 1.2.2, 1.2.3, 1.2.4, 1.1.2, 2.1.1, 2.2.1, 2.2.2, 2.2.3, 1.1.3, 2.3.1, 2.4.1, 3.3.1 or 1.5.1:
  • the invention also relates to multimers of the compounds described herein. These are characterized by being obtainable by dimerization or multimerization of at least two compounds according to the invention, for example the compounds of the formulas (I), (II), (IV) - (XX).
  • At least one R x in one of C0 2 R x , R C0 2 R x , COR x , S0 2 R x and P (0) (R x ) 2 is a bivalent or multivalent group containing the corresponding Link linked with another compound according to the invention.
  • R x may also be an aryl or alkenyl group as defined herein, with the difference being bi- or multivalent. Examples of such compounds are:
  • R is the R x in one of the radicals C0 2 R x , R C0 2 R x , COR x , S0 2 R x and P (0) (R x ) 2 and R 2 is the radical of the compound of the respective formula (I ), (II) or (IV). Particular preference is given to dimers of the compounds of the formulas 1.1.1 and 2.2.2, as shown above in c) and d).
  • R ie the R x of the carboxyl group
  • di- and trimers especially dimers.
  • dimers especially dimers.
  • all particular embodiments disclosed herein in the context of the monomeric compounds of the invention are equally applicable to the dimers and multimers, and vice versa.
  • Figure 1 shows an exemplary comparison of absorbance and photoluminescence of the acceptor molecules disclosed herein, donor molecules, and emitter molecules composed thereof.
  • Figure 1 a shows absorption and photoluminescence of the acceptor methyl 2-aminobenzoate (2), the donor dimethylacridine (5), and the emitter (IV-5).
  • the compounds were embedded in each case in a concentration of 2 wt .-% in polystyrene and carried out the measurements with the resulting thin films.
  • emission was measured in different polar solvents for the emitter (IV-5).
  • the CT character of the emitter (IV-5) is shown by the typical red shift of its emission with increasingly polar solvent.
  • FIG. 1 b shows the comparison of the absorption and photoluminescence of methyl 2-aminobenzoate (2) and the emitter (IV-5).
  • the excitation in this case was 275 nm to allow emission from both channels.
  • the principle of enhancing the internal CT character of the benzoate acceptor becomes apparent.
  • the emission spectrum of the pure methyl 2-aminobenzoate (2) shows, dual fluorescence is present.
  • the attachment of the dimethylacridine donor group to the benzoate acceptor significantly enhances CT emission while decreasing local singlet emission.
  • T room temperature
  • the prompt component was integrated after a delay of 2.25 ns with respect to the excitation pulse over 1 .7 ns.
  • the delayed emission was integrated after 1 ⁇ is over 1 ⁇ is.
  • the prompt component was integrated after a delay of 2.25 ns with respect to the excitation pulse over 1 .7 ns.
  • the delayed emission was integrated after 1 ⁇ is over 1 ⁇ is.
  • the present invention further relates to the use of at least one compound of the formula (I) or the specific embodiments disclosed herein in an optoelectronic component, for example an organic electroluminescent device (OLED), an organic integrated circuit (O-IC), an organic field Effect transistor (O-FET), an organic thin film transistor (O-TFT), an organic light emitting transistor (O-LET), an organic solar cell (O-SC), an organic optical detector, a organic photoreceptor, an organic field quench device (O-FQD), a light emitting electrochemical cell (LEC) or an organic laser diode (O-laser) each as an emitter material, or as a material in which thermal activation activates the triplet excitations into singlet excitations These singlets are then used to excite other embedded singlet emitters.
  • OLED organic electroluminescent device
  • O-IC organic integrated circuit
  • O-FET organic field Effect transistor
  • OFTFT organic thin film transistor
  • OF-LET organic light emitting transistor
  • O-SC
  • the compounds of formula (I) as defined herein or the specific embodiments of the compounds disclosed herein are used as emitter material in the aforementioned optoelectronic devices.
  • the present invention furthermore relates to an optoelectronic component comprising at least one compound as described herein or at least one of the specific embodiments of the compounds disclosed herein.
  • the optoelectronic device contains at least one compound as described herein, wherein the compound of general structural formula (I) emits electromagnetic radiation having a wavelength of 380 nm to 750 nm, or the compound of general structural formula (I) its singlet excitations to another transmits fluorescent emitter emitting at a wavelength of 380 nm to 750 nm.
  • the emission of the compound of the general structural formula (I) or of the further fluorescent emitter takes place predominantly in the blue spectral range from 400 nm to 480 nm. In other embodiments, the emission of the compound of the general structural formula (I) or of the further fluorescent emitter takes place predominantly in the green spectral range from 480 nm to 580 nm. In still other embodiments, the emission of the compound of the general structural formula (I) or of the further fluorescent emitter takes place predominantly in the red spectral range from 580 nm to 750 nm.
  • the optoelectronic device is OSCs having a photoactive organic layer.
  • This photoactive layer includes low molecular weight compounds, oligomers, polymers or mixtures thereof as organic coating materials.
  • a preferably opaque or semitransparent electrode is applied as the cover contact layer.
  • the optoelectronic component is arranged on a flexibly designed substrate.
  • a flexible substrate is understood to be a substrate which ensures deformability as a result of external forces.
  • flexible substrates are also suitable for mounting on curved surfaces.
  • Flexible substrates include, but are not limited to, plastic or metal foils.
  • the coating is carried out for producing an optoelectronic component by means of vacuum processing of organic compounds according to the invention, so that advantageously can be dispensed for the production of optoelectronic device high temperature steps above 160 ° C, preferably the deposition at substrate temperatures below 90 ° C, more preferably at below 30 ° C.
  • the compounds used according to the invention for producing the optoelectronic component have a low evaporation temperature, preferably ⁇ 300 ° C., particularly preferably ⁇ 250 ° C. In various embodiments, however, the evaporation temperature is at least 120 ° C. It is particularly advantageous if the organic compounds according to the invention are sublimable in a high vacuum.
  • the coating for producing an optoelectronic component takes place by means of solvent processing of the compounds described herein.
  • the availability of commercial spray robots makes this application process easily scalable to industry roll-to-roll standards.
  • the optoelectronic component in the sense of the present invention is a generic solar cell.
  • Such an optoelectronic component usually has a layer structure, wherein the respectively lowest and uppermost layer are formed as an electrode and counter electrode for electrical contacting.
  • the optoelectronic component is arranged on a substrate, such as, for example, glass, plastic (PET, etc.) or a metal strip.
  • At least one organic layer comprising at least one organic compound is arranged between the substrate-near electrode and the counterelectrode.
  • Organic compounds which may be used here are organic low molecular weight compounds, oligomers, polymers or mixtures.
  • the organic layer is a photoactive layer.
  • the optoelectronic component is designed as a tandem or multiple component. In this case, at least two optoelectronic components are deposited as a layer system one above the other. On or under the trained as contact basic and In various embodiments, cover layers may be followed by additional layers for coating or encapsulating the component or other components.
  • the organic layer is formed as one or more thin layers of vacuum-processed low molecular weight compounds or organic polymers.
  • vacuum-processed low molecular compounds and polymers based optoelectronic devices are known in the art (Walzer et al., Chemical reviews 2007, 107 (4), 1233-1271, Peumans et al., J. Appl. Phys , 93 (7), 3693-3722).
  • the organic layer is deposited on a substrate using vacuum processable compounds of the inventive compounds described herein.
  • the organic layer is wet-chemically deposited on a substrate using solutions.
  • the compound of the invention in various embodiments is selected from the group consisting of compounds of the formula (I) as defined herein, in particular compounds of the formulas (IV-1), (IV-2), (IV-3), ( IV-4), (IV-5) and (IV-6) as defined herein.
  • the optoelectronic device containing at least one of the compounds of formula (I) as described herein is an organic light emitting diode (OLED).
  • OLED organic light emitting diode
  • the OLEDs according to the invention are basically composed of several layers, for example:
  • the OLED does not have all of the mentioned layers, for example, an OLED having the layers (1.) (anode), (3.) (light-emitting layer), and (6.) (cathode) is also in which the functions of the layers (2) (hole conductor layer) and (4) (hole / exciton layer layer) and (5) (electron conductor layer) are taken over by the adjacent layers.
  • OLEDs containing the layers (1.), (2.), (3.) and (6.) or the layers (1.), (3.), (4.), (5.) and (6 .) are also suitable.
  • the OLEDs between the anode (1.) and the hole conductor layer (2.) or between (2.) and (3.) have a block layer for electrons / excitons.
  • the compounds of the formula (I) can be used as emitter or matrix materials in the light-emitting layer.
  • the compounds of the formula (I) can be present in the light-emitting layer as the sole emitter and / or matrix material-without further additives. However, it is likewise possible that, in addition to the compounds of the formula (I) used according to the invention, further compounds are present in the light-emitting layer. For example, one or more fluorescent dyes may be present to alter the emission color of the emitter molecule present.
  • the individual of the abovementioned layers of the OLED can in turn be composed of 2 or more layers.
  • the hole-transporting layer may be composed of a layer into which holes are injected from the electrode and a layer that transports the holes away from the hole-injecting layer into the light-emitting layer.
  • the electron-transporting layer may also consist of several layers, for example a layer in which electrons are injected through the electrode and a layer which receives electrons from the electron-injecting layer and transports them into the light-emitting layer. These mentioned layers are selected in each case according to criteria such as energy level, temperature resistance and charge carrier mobility, as well as energy difference of said layers with the organic layers or the metal electrodes.
  • the person skilled in the art is able to choose the structure of the OLEDs in such a way that it is optimally adapted to the organic compounds used according to the invention as emitter substances.
  • the HOMO (highest occupied molecular orbital) of the hole-transposing layer should be aligned with the work function of the anode and the LUMO (lowest unoccupied molecular orbital) of the electron-transporting layer should be aligned with the work function of the cathode.
  • the anode (1) is an electrode that provides positive charge carriers.
  • it may be constructed of materials including a metal, a mixture of various metals, a metal alloy, a metal oxide, or a mixture of various metal oxides.
  • the anode may be a conductive polymer. Suitable metals include the metals of groups 11, 4 and 5 of the Periodic Table of the Elements and the transition metals of groups 9 and 10.
  • mixed metal oxides of groups 12, 13 and 14 of the Periodic Table of the Elements are generally used , for example indium tin oxide (ITO).
  • ITO indium tin oxide
  • the anode (1) contains an organic material, for example polyaniline, as described, for example, in Nature, Vol. 357, 477-479 (1992). At least either the anode or the cathode should be at least partially transparent in order to be able to decouple the light formed.
  • the material used for the anode (1.) is preferably ITO.
  • Suitable hole conductor materials for the layer (2) of the OLEDs according to the invention are disclosed, for example, in Kirk-Othmer Encyclopedia of Chemical Technology, 4th Edition, Vol. 18, pages 837 to 860, 1996. Both hole transporting molecules and polymers can be used as hole transport material.
  • Commonly used hole-transporting molecules are selected from the group consisting of tris- [N- (1-naphthyl) -N- (phenylamino)] triphenylamine (1-naphDATA), 4,4'-bis [N- (1-naphthyl) -N-phenyl-amino] biphenyl ( ⁇ -NPD), N, N'-diphenyl-N, N'-bis (3-methylphenyl) - [1, 1'-biphenyi] -4,4'-diamine (TPD ), 1, 1-bis [(di-4-tolylamino) phenyl] cyclohexane (TAPC), N, N'-bis (4-meihylphenyl) -N, N'-bis (4-ethylphenyl) - [1, r- (3,3'-dimethyl) biphenyl] -4,4'-diamine (ETPD), tetrakis-
  • hole-transporting polymers are selected from the group consisting of polyvinylcarbazoien, (phenyidimethyl) polysilanes and Poiyaniiinen. It is also possible to obtain hole transporting polymers by doping hole transporting molecules into polymers such as polystyrene and polycarbonate. Suitable hole-transporting molecules are the molecules already mentioned above.
  • carbene complexes can be used as hole conductor materials, wherein the band gap of the at least one hole conductor material is generally greater than the band gap of the emitter material used.
  • band gap is to be understood as the triplet energy.
  • Suitable carbene complexes are e.g. Carbene complexes, as described in WO 2005/019373 A2, WO 2006/056418 A2 and WO 2005/1 13704 and in the older, not previously published European applications EP 061 12228.9 and EP 061 12198.4.
  • the light-emitting layer (3) contains at least one emitter material.
  • it may be a fluorescence or phosphorescence emitter, suitable emitter materials being known to the person skilled in the art.
  • the at least one emitter material is a fluorescent emitter having a strong delayed component or a phosphorescence emitter.
  • At least one of the emitter materials contained in the light-emitting layer (3) is a compound of the formula (I) as described herein.
  • at least one compound of the formula (I) can additionally be used as matrix material.
  • the block layer for holes / excitons (4) can typically comprise hole blocker materials used in OLEDs, such as 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline (bathocuproine, (BCP)), bis (2-methyl 8-quinolinato) -4-phenyl-phenylatoaluminum (lil) (BAIq), phenothiazine S, S-dioxide derivatives and 1,3,5-tris (N-phenyl-2-benzylimidazole) -benzene) (TPBI) where TPBI and BAIq are also suitable as electron-conducting materials.
  • BCP 2,9-dimethyl-4,7-diphenyl-1,10-phenanthroline
  • BAIq bis (2-methyl 8-quinolinato) -4-phenyl-phenylatoaluminum
  • TPBI phenothiazine S, S-dioxide derivatives and 1,3,5-tris (N-pheny
  • compounds containing aromatic or heteroaromatic groups containing carbonyl groups via groups as disclosed in WO2006 / 100298 can be used as a blocking layer for holes / excitons (4) or as matrix materials in the light-emitting layer (FIG. 3.) are used.
  • the present invention relates to an OLED according to the invention comprising the layers (1.) anode, (2.) hole conductor layer, (3.) light-emitting layer, (4.) block layer for holes / excitons, (5.) electron conductor layer and (6.) Cathode, and optionally further layers, wherein the light-emitting layer (3.) contains at least one compound of formula (I).
  • suitable Eiekt Ronbergerite materials are TPBI and BAIq.
  • hole conductor materials and electron conductor materials some may fulfill several functions.
  • some of the electron-conducting materials are simultaneously hole-blocking materials if they have a deep HOMO. These can be z. B. in the block layer for holes / excitons (4th) are used.
  • the function as a hole / exciton blocker of the layer (5.) is taken over, so that the layer (4.) can be omitted.
  • the charge transport layers can also be electronically doped in order to improve the transport properties of the materials used, on the one hand to make the layer thicknesses more generous (avoidance of pinholes / short circuits) and on the other hand to minimize the operating voltage of the device.
  • the hole conductor materials can be doped with electron acceptors, for example phthalocyanines or arylamines such as TPD or TDTA can be doped with tetrafluorotetracyanchinodimethane (F4-TCNQ).
  • the electron conductor materials may be doped, for example, with alkali metals, for example Alqn with lithium.
  • the electronic doping is known to the person skilled in the art and described, for example, in W. Gao, A. Kahn, J.
  • the cathode (6) is an electrode for introducing electrons or negative charge carriers.
  • Suitable materials for the cathode are selected from the group consisting of alkali metals of group Ia, for example Li, Cs, alkaline earth metals of group IIa, for example calcium, barium or magnesium, metals of group IIb of the Periodic Table of the Elements (old ILJPAC version) comprising the lanthanides and actinides, for example samarium.
  • metals such as aluminum or indium, as well as combinations of all the metals mentioned can be used.
  • lithium-containing organometallic compounds or LiF can be applied between the organic layer and the cathode to reduce the operating voltage.
  • the OLED according to the present invention may additionally contain further layers which are known to the person skilled in the art.
  • a layer can be applied between the layer (2) and the light-emitting layer (3), which facilitates the transport of the positive charge and / or adapts the band gap of the layers to one another.
  • this further layer can serve as a protective layer.
  • additional layers may be present between the light-emitting layer (3) and the layer (4) to facilitate the transport of the negative charge and / or to match the bandgap between the layers.
  • this layer can serve as a protective layer.
  • the OLED according to the invention contains at least one of the further layers mentioned below: A hole injection layer between the anode (1.) and the hole-transporting layer (2.); a block layer for electrons between the hole-transposing layer (2) and the light-emitting layer (3); an electron injection layer between the electron-transporting layer (5) and the cathode (6).
  • Suitable materials for the individual layers are known to those skilled in the art and e.g. in WO 00/70655.
  • the layers used in the OLED according to the invention are surface-treated in order to increase the efficiency of the charge carrier transport.
  • the selection of the materials for each of said layers is preferably determined by obtaining an OLED having a high efficiency and lifetime.
  • the preparation of the OLEDs according to the invention can be carried out by methods known to the person skilled in the art.
  • the inventive OLED is produced by sequential vapor deposition (vapor deposition) of the individual layers onto a suitable substrate.
  • Suitable substrates are for example glass, inorganic semiconductors or polymer films.
  • vapor deposition conventional techniques can be used such as thermal evaporation, chemical vapor deposition (CVD), physical vapor deposition (PVD) and others.
  • the organic layers of the OLED can be applied from solutions or dispersions in suitable solvents using coating techniques known to those skilled in the art.
  • the various layers have the following thicknesses: anode (1.) 50 to 500 nm, preferably 100 to 200 nm; Hole-conducting layer (2) 5 to 100 nm, preferably 20 to 80 nm, light-emitting layer (3) 1 to 100 nm, preferably 10 to 80 nm, block layer for holes / excitons (4) 2 to 100 nm, preferably 5 to 50 nm, electron-conducting layer (5) 5 to 100 nm, preferably 20 to 80 nm, cathode (6) 20 to 1000 nm, preferably 30 to 500 nm.
  • the ratio of the layer thicknesses of the individual layers in the OLED depends on the materials used.
  • the layer thicknesses of optionally used additional layers are known to the person skilled in the art. It is possible that the electron-conducting layer and / or the hole-conducting layer have larger thicknesses than the indicated layer thicknesses when they are electrically doped.
  • the light-emitting layer and / or at least one of the further layers optionally present in the OLED according to the invention contains at least one compound of the general formula (I). While the at least one compound of the general formula (I) is present in the light-emitting layer as emitter and / or matrix material, the at least one compound of the general formula (I) in the at least one further layer of the inventive OLED can each alone or together with at least one of the other suitable for the corresponding layers above materials are used. It is also possible for the light-emitting layer to contain, in addition to the compound of the formula (I), one or more further emitter and / or matrix materials.
  • the efficiency of the OLEDs of the invention may be e.g. be improved by optimizing the individual layers.
  • highly efficient cathodes such as Ca or Ba, optionally in combination with an intermediate layer of LiF, can be used.
  • Shaped substrates and new hole-transporting materials that bring about a reduction in the operating voltage or an increase in quantum efficiency are also usable in the OLEDs according to the invention.
  • additional layers may be present in the OLEDs to adjust the energy levels of the various layers and to facilitate electroluminescence.
  • the OLEDs according to the invention can be used in all devices in which electroluminescence is useful. Suitable devices are preferably selected from stationary and mobile screens and lighting units. Stationary screens are e.g. Screens of computers, televisions, screens in printers, kitchen appliances and billboards, lights and signboards. Mobile screens are e.g. Screens in cell phones, laptops, digital cameras, vehicles, and destination displays on buses and trains.
  • the compounds of the formula (I) can be used in various embodiments in OLEDs with inverse structure.
  • the construction of inverse OLEDs and the materials usually used therein are known to the person skilled in the art.
  • methyl 2-aminobenzoate (2) (15 g, 0.10 mol), bromobenzene (15.6 g, 0.10 mol), Pd (OAc) 2 , (0.45 g, 2.02 mmol), K 2 CO 3 (27 g, 0.202 mol), BIN AP (1.25 g, 2.02 mmol) and 50 mL toluene under argon.
  • the mixture was stirred at 70 ° C overnight. After cooling, the inorganic residues were filtered off and the solution was evaporated.
  • the resulting diazonium salt was cooled to -5 ° C over 10 minutes and then to a preheated to 40 ° C mixture of 22.4 g Kl solution in 40 ml of distilled water, 6.5 g of sodium hydrosulfite and concentrated sulfuric acid in a 500 ml Three-necked round bottom flask with reflux condenser added. This mixture was stirred at 40 ° C for 5 minutes and then at 80 ° C for one hour. The black reaction mixture was cooled to room temperature and rinsed with 20 mL of 20% H2SO4, 20 mL NaHSCU, water and brine. The separated organic phase was diluted with 30 ml of ethyl acetate, dried over MgSO4, filtered off and completely evaporated. The yield was 26 g (76%) of orange methyl 2-iodobenzoate (6).
  • Phenothiazine (1, 52 g, 7.6 mmol), methyl 2-iodobenzoate (6) (2 g, 7.6 mmol), activated K 2 CO 3 (1, 06 g, 7.6 mmol) and dichlorobenzene (25 mL) were added to a 100 ml Schlenk flask.
  • the reaction mixture was deoxygenated several times with a vacuum pump before adding Cu (0.96 g, 15.2 mmol) and Cul (0.06 g, 0.3 mmol) under N 2 atmosphere. Subsequently, the reaction mixture was stirred for 12 hours at 190 ° C and filtered. The remaining solid was washed with toluene and the mixture was concentrated under reduced pressure.
  • the viscous crude product was dissolved in 20 ml of diethyl ether and crystallized overnight. The resulting yellow crystals were washed with acetone tril, after which the yield was 1.54 g (61%).

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Abstract

La présente invention concerne des composés comprenant au moins un groupe donneur et au moins un groupe accepteur, tels que décrits dans la description, qui se distinguent par un caractère de transfert de charge (CT) prononcé, ainsi que leur utilisation comme émetteur dans une pièce optoélectronique.
PCT/EP2017/064689 2016-06-15 2017-06-15 Molécule émettrice à base d'accepteurs à double fluorescence de type benzène-(poly)carboxylate Ceased WO2017216299A1 (fr)

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CN110407710A (zh) * 2018-04-28 2019-11-05 香港科技大学深圳研究院 一种三苯胺衍生物类的纯有机室温磷光材料及其制备方法
CN110818652A (zh) * 2018-08-09 2020-02-21 上海和辉光电有限公司 一种含芳基酯衍生物的有机发光材料、其制备方法及其应用
JPWO2020189283A1 (fr) * 2019-03-18 2020-09-24
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