WO2016116525A1 - Molécules organiques, notamment pour une utilisation dans des composants opto-électroniques - Google Patents

Molécules organiques, notamment pour une utilisation dans des composants opto-électroniques Download PDF

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WO2016116525A1
WO2016116525A1 PCT/EP2016/051167 EP2016051167W WO2016116525A1 WO 2016116525 A1 WO2016116525 A1 WO 2016116525A1 EP 2016051167 W EP2016051167 W EP 2016051167W WO 2016116525 A1 WO2016116525 A1 WO 2016116525A1
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group
substituted
radicals
aromatic
formula
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David Ambrosek
Michael Danz
Harald FLÜGGE
Jana Friedrichs
Tobias Grab
Andreas Jacob
Stefan Seifermann
Daniel Volz
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Cynora Gmbh
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Definitions

  • the invention relates to purely organic molecules and their use in organic light-emitting diodes (OLEDs) and in other optoelectronic components.
  • OLED organic light-emitting diodes
  • OLEDs are usually realized in layer structures, which consist predominantly of organic materials.
  • layer structures consist predominantly of organic materials.
  • FIG. 1 The heart of such components is the emitter layer, in which usually emitting molecules are embedded in a matrix.
  • the energy contained in the excitons can be emitted by the corresponding emitters in the form of light, in this case speaking of electroluminescence.
  • An overview of the function of OLEDs can be found, for example, in H. Yersin, Top. Curr. Chem., 2004, 241, 1 and H. Yersin, "Highly Efficient OLEDs with Phosphorescent Materials”; Wiley-VCH, Weinheim, Germany, 2008.
  • a new generation of OLEDs is based on the utilization of delayed fluorescence (TADF: thermally activated delayed fluorescence or singlet harvesting).
  • TADF thermally activated delayed fluorescence or singlet harvesting
  • Cu (I) complexes can be used, which can thermally revert to a singlet state due to a small energy gap between the lowest triplet state ⁇ and the overlying singlet state Si (AE (Si-Ti) triplet exitones
  • AE (Si-Ti) triplet exitones In addition to the use of transition-metal complexes, purely organic molecules (ie without metal ion) can exploit this effect.
  • the invention relates to purely organic molecules which can be used in optoelectronic components.
  • Such organic molecules have a structure of the formula 1 or have a structure of the formula 1:
  • n 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 or 14;
  • n O, 1,2,3,4,5,6,7,8,9,10,1,1,12,13 or 14;
  • Q an sp2 or sp3 hybridized main group element of groups 14, 15 or 16 of the Periodic Table of the Chemical Elements, in particular carbon, silicon, germanium, nitrogen, phosphorus, arsenic, oxygen or sulfur corresponding to their valencies with further radicals R ** can be substituted.
  • Q may be an aromatic system having 6 aromatic ring atoms (eg, phenyl) or part of an aromatic system having 10 to 40 aromatic ring atoms (e.g., naphthyl or anthracenyl) which may be substituted by one or more of R **, or also a combination of these systems.
  • R ** is either a radical R * or a chemical entity AF, wherein in formula 1 at least two different units AF must be contained;
  • R 3 is independently selected for each occurrence from the group consisting of H, deuterium, phenyl, naphthyl, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H Atoms may be replaced by F or CF 3 ; two or more substituents R 3 may also together form a mono- or polycyclic, aliphatic ring system.
  • N0 2 may be replaced, or an aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, each of which may be substituted by one or more radicals R 9 , or an aryloxy or heteroaryloxy group having 5 to 60 aromatic ring atoms, which may be substituted by one or more radicals R 9 , or a Diarylamino group, diheteroarylamino group or arylheteroarylamino group having 10 to 40 aromatic ring atoms which may be substituted by one or more of R 3 , or a combination of these systems; two or more of these substituents R 7 may also together form a mono- or polycyclic, aliphatic, aromatic and / or benzoannellated ring system;
  • R 8 is independently selected in each occurrence from the group consisting of H, deuterium, phenyl, naphthyl, F, CF 3 or an aliphatic, aromatic and / or heteroaromatic hydrocarbon radical having 1 to 20 carbon atoms, in which also one or more H atoms can be replaced by F or CF 3 ; two or more substituents R 8 may also together form a mono- or polycyclic, aliphatic ring system.
  • An aryl group in the sense of this invention contains 6 to 60 aromatic ring atoms;
  • a heteroaryl group contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
  • the heteroatoms are in particular N, O, and S. If in the description of the present invention other definitions are given which deviate therefrom, for example with regard to the number of aromatic ring atoms or the heteroatoms contained therein, these deviating definitions apply.
  • An aryl group or heteroaryl group is understood to mean a simple aromatic cycle, ie benzene, or a simple heteroaromatic cycle, for example pyridine, pyrimidine or thiophene, or a heteroaromatic polycycle, for example naphthalene, phenanthrene, quinoline or carbazole.
  • a condensed (fused) aromatic or heteroaromatic polycycle consists in the context of the present application of two or more fused simple aromatic or heteroaromatic cycles.
  • An aryl or heteroaryl group which may be substituted in each case by the abovementioned radicals and which may be linked via any position on the aromatic or heteroaromatic compounds is understood in particular to mean groups which are derived from benzene, naphthalene, anthracene, phenanthrene, pyrene, Dihydropyrenes, chrysene, perylene, fluoranthene, benzanthracene, benzphenanthrene, tetracene, pentacene, benzpyrene, furan, benzofuran, isobenzofuran, dibenzofuran, thiophene, benzothiophene, isobenzothiophene, dibenzothiophene; Pyrrole, indole, isoindole, carbazole, pyridine, quinoline, isoquinoline, acridine, phenanthridine, benzo-5,6-quinoline, isoquinoline
  • An aromatic ring system in the sense of this invention contains 6 to 60 carbon atoms in the ring system.
  • a heteroaromatic ring system in the context of this invention contains 5 to 60 aromatic ring atoms, at least one of which represents a heteroatom.
  • the heteroatoms are in particular selected from, N, O and / or S.
  • An aromatic or heteroaromatic ring system in the sense of this invention is to be understood as meaning a system which does not necessarily contain only aryl or heteroaryl groups but in which also several aryl or heteroaryl groups by a non-aromatic moiety (in particular less than 10% of the different atoms), such as a sp3 -hybridized.
  • C, Si, or N atom an sp 2 -hybridized.
  • C, N, or O atom or a sp-hybridized C atom.
  • systems such as 9, 10-T-diarylfluorene, triarylamine, diaryl ethers, stilbene, etc. are also to be understood as aromatic ring systems in the context of this invention, and systems in which two or more aryl groups are exemplified by a linear or cyclic alkyl, alkenyl or alkynyl groups or by a silyl group.
  • systems in which two or more aryl or heteroyrayl groups are linked together via single bonds are understood as aromatic or heteroaromatic ring systems in the context of this invention, such as systems such as biphenyl, terphenyl or diphenyltriazine.
  • aromatic or heteroaromatic ring system having 5 to 60 aromatic ring atoms, which may be substituted in each case with radicals as defined above and which may be linked via any positions on the aromatic or heteroaromatic, are understood in particular groups which are derived from benzene, naphthalene , Anthracene, benzanthracene, phenanthrene, benzphenanthrene, pyrene, chrysene, perylene, fluoranthene, naphthacene, pentacene, benzpyrene, biphenyl, biphenylene, terphenyl, terphenyls, quaterphenyl, fluorene, spirobifluorene, dihydrophenanthrene, dihydropyrene, tetrahydro-pyrene, cis- or trans- indenofluorene, truxene, isotruxene, spirotruxene, spiroiso
  • AF Organic chemical entity (remainder). There are at least two different chemical entities AF1 and AF2 included; AF1: a first chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ electrons (eg in the form of at least one aromatic system); AF2: a second chemical entity comprising a conjugated system, in particular at least six conjugated ⁇ -electrons (eg in the form of at least one aromatic system); AF2 always has a lower (mathematical) HOMO value compared to AF1 (and correspondingly a lower LUMO number than AF1).
  • the molecules according to the invention have the features that
  • the chemical entities AF1 and AF2 are linked to one another such that the electronic communication between them is interrupted. This disruption is characterized by localization of the HOMO and LUMO frontier orbits on separate parts of the molecule, allowing for a charge-transfer transition.
  • the chemical units AF1 and AF2 are connected to one another via a separator such that the electronic communication between them is interrupted, which is characterized by the localization of the frontier orbitals HOMO and LUMO on separate parts of the molecule.
  • the separator may have any structure as long as an interruption of the electronic communication is ensured.
  • the energy values HOMO (AF1), HOMO (AF2), LUMO (AF1), LUMO (AF2) are calculated using the density functional theory (DFT), whereby the attachment positions of the ambifunctional units and the separators are saturated with a hydrogen atom according to their chemical valences.
  • DFT density functional theory
  • the limits given refer to orbital energies in eV calculated with the BP86 functional (Becke, A.D. Phys Rev. A1988, 38, 3098-3100, Perdew, J.P. Phys. Rev. B1986, 33, 8822-8827).
  • the electronic communication between the two chemical entities AF1 and AF2 via conjugated bonds with an optional separator is disrupted when the frontier orbitals HOMO and LUMO are located on separate parts of the molecule, allowing for a charge-transfer transition.
  • the localization of the frontier orbitals HOMO or LUMO is determined using the density functional theory (DFT) with the BP86 functional (Becke, AD Phys.Rev.A1988, 38, 3098-3100, Perdew, JP Phys. Rev. B1986, 33, 8822-8827 ):
  • the single electron wave function calculates the single electron density by squaring and integrates it over the space occupied by the part of the molecule.
  • This space can be determined from the atomic coordinates and van der Waals radii of the atoms.
  • the resulting number corresponds to the proportion of orbital on the moiety.
  • a majority separation of the frontier orbitals corresponds to an overlap parameter O in the range 0, 1-20% to allow a charge-transfer transition.
  • ) b results from the integral over the entire space over the respective smaller value of the squared wave function:
  • the organic molecules have a structure of the formula 2a to 2d or have a structure of the formula 2a to 2d, wherein the definitions given in formula 1 apply and the organic molecule has at least two different units AF.
  • o is the numerical value 0, 1, 2, 3 or 4 and o 'can take the numerical value 0, 1, 2, 3, wherein at least two different AF must be present in the molecule.
  • Y or Y ' independently and identically on each occurrence are identically or differently a chemical entity AF, t-butyl, phenyl, naphthyl or a linear or cyclic alkyl, alkenyl, alkynyl, alkoxy or thioalkoxy group, these containing the phenyl moiety, to which they are bound can form a finned system.
  • organic molecules are selected from:
  • n ' is 1, 2 or 3, depending on the number of positions which can be substituted by R * or R ** on the ring, if up to three positions are substitutable on the ring or n' is 1, 2, 3, or 4 is, provided that up to four positions are substitutable on the ring;
  • organic molecules are selected from the following group of molecules:
  • an organic molecule in some embodiments has multiple identical AFs.
  • separator S The part of the organic molecule according to formula 1, formula 2a to formula 2d or of formulas 2-1 to 2-22, which represents non-chemical units AF, is also referred to as separator S.
  • separator S If the AF is precipitated in formulas 1 and 2a to 2d or 2-1 to 2-22, the molecular fragments remain, which are referred to here as separator S.
  • the separator is a molecular fragment having one of the following structures, where # denotes the location at which the AF is bound to the separator, R ** is the same as a radical R *, or denotes the location at which an AF is connected to the separator, and otherwise the definitions given in formulas 2-1 to 2-19 apply:
  • n ' is 1, 2 or 3, depending on the number of positions which can be substituted by R * or R ** on the ring, if up to three positions are substitutable on the ring or n' is 1, 2, 3, or 4 is, provided that up to four positions are substitutable on the ring;
  • the separator S is selected from the group consisting of the following structures:
  • the separator S distinguishes the organic molecules of molecules according to the prior art by the type of separation of AFs (or donors and acceptors) shown here.
  • AFs or donors and acceptors
  • Known organic emitters usually consist of directly linked chemical units.
  • a separation of the conjugated aromatic systems does not take place therein, especially in connection with the localization of HOMO and LUMO on separate parts of the molecule.
  • Separators serve to interrupt the electronic communication between the chemical units AF1 and AF2 by linking the units such that the frontier orbitals HOMO and LUMO lie on mostly separate parts of the molecule, which need not necessarily be the case without the separator.
  • separators do not significantly alter the position of the HOMO or LUMO of the AFs shown in Table 1. Not significant in the context of this invention is a change of not more than +/- 0.4 eV. The calculation of such energies is known and works according to the manner described above by DFT calculation.
  • spectroscopic selection rules symmetric molecules
  • UV / VIS spectroscopy UV / VIS spectroscopy
  • quantum chemical calculation of the oscillator strength it can be predicted whether a quantum mechanical transition is allowed.
  • the goal is a decay time of ⁇ 50 ps. With a long decay time of the (organic) emitter, saturation effects quickly occur at high current intensities, which adversely affects the component lifetime and prevents the achievement of high brightness levels.
  • a measure of the decay time is the quantum mechanical overlap integral, which is approximately represented by the overlap parameter O defined above.
  • the smaller the overlap integral the more separated the frontier orbitals HOMO and LUMO, and the more likely the charge-transfer transition. However it sinks equally the probability of TADF emission due to decreasing oscillator strengths.
  • the overlap integral must be adjusted.
  • the desired overlap is achieved by the separator S.
  • a measure of the decay time is the AE (Si-T-i) distance. This is influenced by the overlap of HOMO and LUMO.
  • the size of the quantum mechanical overlap integral which can be calculated by the above-mentioned DFT method, can be controlled in a targeted manner by selecting the separator. If it comes to the complete separation of HOMO and LUMO this has a value of 0. The probability of an efficient emission of the organic molecule decreases drastically. At a value of 1, there is no longer delayed fluorescence (TADF) but spontaneous emission.
  • TADF delayed fluorescence
  • separators S shown here fulfill two functional features (see FIG.
  • the HOMO energy is lower than the HOMO energy of the donor chemical unit AF and
  • the LUMO energy is higher than the LUMO energy of the acceptor chemical entity AF.
  • the unit AF1 has a structure of sub-formula 1 or has a structure of sub-formula 1
  • VG3 bridging group is independently selected from the group consisting of each occurrence
  • N, O, S, CR **, C an element-element single bond between X and Y or between X and K, where not 2 units VG3 are simultaneously an element-element single bond between X and Y and between X and K. .
  • Z is independently CR ** or N at each occurrence; and wherein at most 4 of the units VG3, K, X, Y, Z are simultaneously equal to N;
  • R ** is independently at each occurrence either a radical R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S;
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of the sub-formulas 1.1 to 1.10 or has a structure of the sub-formulas 1.1 to 1.10.
  • Sub-formula 1.8 Sub-formula 1.9 Sub-formula 1.10 and where:
  • R ** is independently at each occurrence either a radical R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S;
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of the sub-formulas 1.1 1 to 1 .13 or has a structure of the sub-formulas 1.1 1 to 1 .13
  • R ** is independently at each occurrence either a residue R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S.
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of sub-formula 1.14 or has a structure of sub-formula 1.14
  • U is CR ** or N, with a maximum of 3 units U being N at the same time, and no adjacent units U being N at the same time;
  • Alk is selected from the group consisting of methyl, ethyl, propyl, / 'so-propyl, butyl, tert-butyl, pentyl, hexyl, 2-ethylhexyl, cyclohexyl, heptyl, octyl, nonyl, decyl, undecyl or dodecyl; R ** is independently at each occurrence either a residue R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S.
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of the sub-formulas 1.15 to 1.22 or has a structure of the sub-formulas 1.15 to 1.22
  • M is selected from the group consisting of H, deuterium, alk, phenyl, pyridyl and CN, with a maximum of 4 M simultaneously being CN; or denotes a chemical bond to a separator S, wherein exactly one M denotes a chemical bond to a separator S.
  • the unit AF1 has a structure of the sub-formulas 1.23 to 1.24 or has a structure of the sub-formulas 1.23 to 1.24
  • Het is NR **, O, S, S0 2 ;
  • R ** is independently at each occurrence either a residue R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S.
  • R * is defined as in Formula 1.
  • the unit AF1 has a structure of the sub-formulas 1 .25 to 1 .36 or has a structure of the sub-formulas 1 .25 to 1.36
  • V is at each occurrence CR ** or N, where at least one unit V is equal to N; and wherein a maximum of two units V are N at a time; and wherein two adjacent units V are not equal to N at a time.
  • R ** is independently at each occurrence either a residue R *, or a chemical bond to a separator S, where exactly one R ** is a chemical bond to a separator S.
  • R * is defined as in Formula 1.
  • unit AF2 has a structure of sub-formula 2 or has a structure of sub-formula 2
  • n 0 or 1
  • n 0 or 1
  • o 0 or 1
  • p is 0 or 1;
  • VG1 bridging group, is selected from the group consisting of
  • VG2 bridging group at each occurrence is independently selected from the group consisting of CR ** 2 , NR **, O, S and a CC single bond, where two units VG2 are not simultaneously equal to one CC single bond;
  • E is selected from the group consisting of NR **, , O and S;
  • R *** is R ** or is selected from the following units, wherein a maximum of two of the radicals R *** are simultaneously one of the following units:
  • R ** is independently a residue R * at each occurrence and / or marks a point of attachment to a separator S, where exactly one R ** is a point of attachment to a separator S.
  • R * is defined as in Formula 1.
  • the unit AF2 has a structure of the sub-formula 3 or has a structure of the sub-formula 3
  • Sub-formula 3 wherein in sub-formula 3: p is 0 or 1;
  • X is CR ** 2 , NR **, oxygen, sulfur, a direct bond, with a maximum of two placeholders X being simultaneously a direct bond, which are not part of the same ring; and, moreover, the definitions given for sub-formula 2 apply.
  • At least one AF2 of the organic molecule has a structure of the formula 4A1-4A7 or has a structure of the formula 4A1 -4A7;
  • X is C (R **) 2 , NR **, oxygen or sulfur; and, moreover, the definitions given for sub-formula 2 apply.
  • the organic molecule has a structure of formula 5 or has a structure of formula 5;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the organic molecule has a structure of formula 6 or has a structure of formula 6;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the organic molecule has a structure of formula 7 or has a structure of formula 7;
  • W is selected from the group consisting of , an elementary
  • X is CR * 2 , NR *, oxygen, sulfur, a direct bond, with a maximum of two wildcards X being simultaneously a direct bond, which are not part of the same ring;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the organic molecule has a structure of the formula 8 or has a structure of the formula 8;
  • V is independent of each occurrence CR * or N, with a maximum of two units V equal to N at each occurrence; and where not two adjacent units
  • X is CR * 2 , NR *, oxygen, sulfur or a direct bond, wherein a maximum of two wildcards X are simultaneously a direct bond, which are not part of the same ring;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the organic molecule has a structure of formula 9 or has a structure of formula 9;
  • V is independent of each occurrence CR * or N, with a maximum of two units V equal to N at each occurrence; and where not two adjacent units
  • X is CR * 2 , NR *, oxygen, sulfur or a direct bond, wherein a maximum of two wildcards X are simultaneously a direct bond, which are not part of the same ring;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the organic molecule has a structure of the formula 10 or has a structure of the formula 10.
  • V is independent of each occurrence CR * or N, with a maximum of two units V equal to N at each occurrence; and where not two adjacent units
  • X is CR * 2 , NR *, oxygen, sulfur or a direct bond, wherein a maximum of two wildcards X are simultaneously a direct bond, which are not part of the same ring;
  • R ' is R * or is selected from the following units, wherein a maximum of two of the radicals R' are simultaneously one of the following units:
  • the chemical moieties AF1 and AF2 are selected from the compounds listed in Table 1, wherein AF1 and AF2 are not identical.
  • a given chemical entity may represent one chemical entity AF1 in one organic molecule and one chemical entity AF2 in another molecule. Provided that two different AFs always occur in one molecule, additional AFs may be identical to the former. Possible connecting points of the chemical unit AF to a separator S are denoted by lowercase letters.
  • Table 1 shows possible attachment positions of the chemical entity AF for linking to a separator S of the molecule according to the invention with lowercase letters a to z.
  • Each aromatic CH and NH bond is optionally substituted with a solubilising and / or a polymerisable R.
  • organic molecules according to the invention are shown in Table 3, which result from the combination of the above-defined pairs of two chemical entities AF1 and AF2, the separator S and the determination of the linkage.
  • Further organic molecules can be obtained by combining said molecular units, wherein at least two different AF are contained in the molecule. Provided that two different AFs always occur in one molecule, additional AFs may be identical to the former.
  • the naming of the molecules is carried out according to the scheme AF-S-AF, with reference to Table 1 for the naming of the chemical entity AF, since the numbers used in Table 1 are also used in Table 3.
  • the two AFs will interact with each other, their respective HOMO and LUMO hunting most closely following the above conditions.
  • Table 3 Organic molecules according to the invention according to the scheme AF-S-AF. In a molecule at least two different AFs are contained, whereby these can be identical starting from values 3 and larger. S is in each case a spacer S selected from the formulas 3-1 to 3 -19. In brackets the values for AHOMO, ALUMO and Gap are given.
  • 53 - S-291 (2.13 1.73 1.42)
  • 53 - S-292 (1.46 1.39 1.76)
  • 53 - S-293 (0.96 1.20 1.95)
  • 53 - S-293 (0.96 1.20 1.95)

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  • Organic Chemistry (AREA)
  • Engineering & Computer Science (AREA)
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  • Physics & Mathematics (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne des molécules organiques, notamment pour une utilisation dans des composants opto-électroniques tels que des OLED. La molécule organique présente selon l'invention une structure de formule 1, Formule 1. Dans ladite formule 1, n est égal à 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 ou 14 ; m est égal à 0, 1, 2, 3, 4, 5, 6, 7, 8, 9, 10, 11, 12, 13 ou 14 ; Q représente un élément du groupe principal hybridé sp2 ou sp3 des groupes 14, 15 ou 16, qui peuvent être substitués par d'autres radicaux R** en fonction de leurs valences ; et dans laquelle Q peut être un système aromatique ayant 6 atomes de cycle aromatique ou une partie d'un système aromatique ayant de 10 à 40 atomes de cycle aromatique, et ce système aromatique peut être substitué par un ou plusieurs radicaux R**, ou bien une combinaison de ces systèmes ; R** est soit un radical R* soit un motif chimique AF, au moins deux AF différents étant présents dans la molécule organique.
PCT/EP2016/051167 2015-01-20 2016-01-20 Molécules organiques, notamment pour une utilisation dans des composants opto-électroniques WO2016116525A1 (fr)

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