WO2016116530A1 - Compositions s'utilisant en particulier dans des composants optoélectroniques - Google Patents

Compositions s'utilisant en particulier dans des composants optoélectroniques Download PDF

Info

Publication number
WO2016116530A1
WO2016116530A1 PCT/EP2016/051172 EP2016051172W WO2016116530A1 WO 2016116530 A1 WO2016116530 A1 WO 2016116530A1 EP 2016051172 W EP2016051172 W EP 2016051172W WO 2016116530 A1 WO2016116530 A1 WO 2016116530A1
Authority
WO
WIPO (PCT)
Prior art keywords
group
poly
atoms
substituted
radicals
Prior art date
Application number
PCT/EP2016/051172
Other languages
German (de)
English (en)
Inventor
David Ambrosek
Michael Danz
Harald FLÜGGE
Jana Friedrichs
Tobias Grab
Andreas Jacob
Stefan Seifermann
Daniel Volz
Original Assignee
Cynora Gmbh
Priority date (The priority date is an assumption and is not a legal conclusion. Google has not performed a legal analysis and makes no representation as to the accuracy of the date listed.)
Filing date
Publication date
Application filed by Cynora Gmbh filed Critical Cynora Gmbh
Priority to DE112016000391.9T priority Critical patent/DE112016000391A5/de
Publication of WO2016116530A1 publication Critical patent/WO2016116530A1/fr

Links

Classifications

    • 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
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F112/02—Monomers containing only one unsaturated aliphatic radical
    • C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F112/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F112/22—Oxygen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F112/02—Monomers containing only one unsaturated aliphatic radical
    • C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F112/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F112/26—Nitrogen
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F112/02—Monomers containing only one unsaturated aliphatic radical
    • C08F112/04—Monomers containing only one unsaturated aliphatic radical containing one ring
    • C08F112/14—Monomers containing only one unsaturated aliphatic radical containing one ring substituted by hetero atoms or groups containing heteroatoms
    • C08F112/30—Sulfur
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F112/00—Homopolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring
    • C08F112/02—Monomers containing only one unsaturated aliphatic radical
    • C08F112/32—Monomers containing only one unsaturated aliphatic radical containing two or more rings
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08L—COMPOSITIONS OF MACROMOLECULAR COMPOUNDS
    • C08L25/00—Compositions of, homopolymers or copolymers of compounds having one or more unsaturated aliphatic radicals, each having only one carbon-to-carbon double bond, and at least one being terminated by an aromatic carbocyclic ring; Compositions of derivatives of such polymers
    • C08L25/18—Homopolymers or copolymers of aromatic monomers containing elements other than carbon and hydrogen
    • 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
    • H10K85/10—Organic polymers or oligomers
    • H10K85/141—Organic polymers or oligomers comprising aliphatic or olefinic chains, e.g. poly N-vinylcarbazol, PVC or PTFE
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08F—MACROMOLECULAR COMPOUNDS OBTAINED BY REACTIONS ONLY INVOLVING CARBON-TO-CARBON UNSATURATED BONDS
    • C08F2438/00—Living radical polymerisation
    • C08F2438/03—Use of a di- or tri-thiocarbonylthio compound, e.g. di- or tri-thioester, di- or tri-thiocarbamate, or a xanthate as chain transfer agent, e.g . Reversible Addition Fragmentation chain Transfer [RAFT] or Macromolecular Design via Interchange of Xanthates [MADIX]
    • 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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1416—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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1425—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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1408—Carbocyclic compounds
    • C09K2211/1433—Carbocyclic compounds bridged by heteroatoms, e.g. N, P, Si or B
    • 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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/145—Heterocyclic containing oxygen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1458—Heterocyclic containing sulfur as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1466—Heterocyclic containing nitrogen as the only heteroatom
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K2211/00—Chemical nature of organic luminescent or tenebrescent compounds
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1475—Heterocyclic containing nitrogen and oxygen as heteroatoms
    • 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
    • C09K2211/14—Macromolecular compounds
    • C09K2211/1441—Heterocyclic
    • C09K2211/1483—Heterocyclic containing nitrogen and sulfur as heteroatoms
    • 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
    • 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
    • Y02P—CLIMATE CHANGE MITIGATION TECHNOLOGIES IN THE PRODUCTION OR PROCESSING OF GOODS
    • Y02P70/00—Climate change mitigation technologies in the production process for final industrial or consumer products
    • Y02P70/50—Manufacturing or production processes characterised by the final manufactured product

Definitions

  • compositions in particular
  • the invention relates to compositions and their use as emitters in OLEDs (organic light emitting diodes) 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, due to a small energy gap between the lowest triplet state ⁇ and the overlying singlet state Si (AE (Si-Ti)), can thermally recombine triplet exitones into a singlet state.
  • AE overlying singlet state Si
  • transition metal complexes purely organic molecules can exploit this effect.
  • Some such TADF materials have already been used in first optoelectronic devices.
  • the TADF materials often do not have sufficient long-term stability, sufficient thermal or sufficient chemical stability to water and oxygen in the optoelectronic components.
  • not all important emission colors are available.
  • some TADF materials are not vaporizable and therefore not suitable for use in commercial optoelectronic devices.
  • some TADF materials do not have matching energy layers to the other materials used in the optoelectronic device (eg, HOMO energies of TADF emitters greater than or equal to -5.9 eV). It is not possible to achieve sufficiently high efficiencies of the optoelectronic components with high current densities or high luminances with all TADF materials.
  • the syntheses of some TADF materials are expensive.
  • the invention relates in one aspect to a homogeneous composition
  • a homogeneous composition comprising purely organic molecules and polymers (dyes) which have no metal atoms and which can be used as emitters in optoelectronic components.
  • “Homogeneous composition” means that there is no disposition in successive layers or the like, so the constituents of the composition are not applied sequentially or are arranged as stacked structures, but are simple, homogeneous mixing systems.
  • Such a composition comprises (or, in one embodiment, consists of) a polymer poly-AF1 and a low molecular weight component AF2 and / or a macromolecular) component poly-AF2, and optionally another low molecular weight or macromolecular component H having host properties and optionally another low molecular weight or macromolecular component M for adjusting the morphological properties, wherein
  • Poly-AF1 polymer substituted with a chemical unit AF1 via a spacer
  • AF2 chemical unit AF2
  • Poly-AF2 organic polymer substituted with a spacer via a spacer; wherein poly-AF1 has a structure of formula 1;
  • 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); where AF1 and AF2 are not identical;
  • the triplet energy of the host material is not less than the energy of the emitter molecule, otherwise quenching may occur.
  • Energy is transferred from the T1 level of the emitter to the T1 level of the host. The determination of these energy values is via standard laboratory methods such as cyclic voltammetry, photoelectron spectroscopy and DFT calculation (E H OMO, E L UMO) and Absorbtionsspektroskopie or DFT calculation (E Ba ndiücke) possible. Energy transfer takes place between host materials and emitters in OLED devices, which can be determined by doping the emitter or emitter composition into the host by means of photoemission spectroscopy.
  • the low molecular weight compound is a class of low molecular weight substances. In general, they form the counter group to larger, high molecular weight substances, eg. B. long-chain polymers. By significantly lower molecular weight and spatial expansion, low molecular weight compounds often have different chemical and physical properties and can therefore be used or processed differently. For the purposes of this invention, these mean compounds which have a molecular weight of at least 150 g / mol and less than 3000 g / mol, particularly in particular less than 1500 g / mol.
  • Macromolecular compounds are very large molecules that consist of repeating, identical or different structural units (basic building blocks) and have a high molecular mass.
  • the basic building blocks are so-called monomers.
  • a macromolecular compound consists of monomers which have a molecular weight of at least 150 g / mol and less than 3000 g / mol, in particular less than 1500 g / mol.
  • the mass of the macromolecules is more than 6000 g / mol, in particular more than 10000 g / mol.
  • the morphology of an optoelectronic component depends on various factors such as the structure and composition of the materials used, the solvents used, such as toluene, chlorobenzene for the preparation, the solvent concentration, the mixing ratios of the materials used, the production parameters such as time, temperature. Many of these parameters are highly dependent on one another and, above all, influence the formation of the mixture of used ones Materials. The aim is to produce an optimal internal structure, ie a thorough mixing of the materials used.
  • the combination of the specially selected chemical units AF1 and AF2 results in a special state upon electrical and / or optical excitation, the singlet-triplet splitting AE (S1-T1) being less than 2500 cm -1 and, consequently, having a particularly low emission decay time of All combinations that meet this requirement are listed in Table 2.
  • the measurement of singlet-triplet splitting can be made by measuring the band gap by photoelectron spectroscopy using standard laboratory techniques.
  • H Host material whose triplet (T1) and singlet (S1) energy levels are higher in energy than the triplet (T1) and singlet (S1) energy levels of the composition.
  • mixtures are poly-AF1 / AF2, poly-AF1 / poly-AF2 or poly-AF1 / AF2, for example
  • the spacer shown in formula 1 and 2 results depending on the type of polymer used; for example, when vinylic polymers such as polyvinylcarbazole are used, the spacer is identical to a single bond; when a polystyrene derivative is used, it is equal to 1,4-phenylene; when a polyvinylbenzyl derivative is used, it is benzyl.
  • the entire unit PS is defined below.
  • the possible chemical units AF1 and AF2 are limited to the structures listed in Table 1 a and 1 b; in particular
  • 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 chemical units AF1 and AF2 are saturated with a hydrogen atom according to their chemical valences.
  • DFT density functional theory
  • the limits given refer to orbital energies in unit eV calculated with the BP86 functional (Becke, AD Phys Rev. A1988, 38, 3098-3100, Perdew, JP Phys Rev. B1986, 33, 8822-8827 ). Not all hypothetical combinations of AFs among themselves fulfill this condition. All combinations that meet these criteria, 9.7% of the hypothetical combinations, are listed in Table 2.
  • the invention also encompasses a composition whose optoelectronic function of light generation results from combining the components poly-AF1 and AF2 or poly-AF2.
  • poly-AF1 and poly-AF2 are used.
  • Table 1a List of possible first chemical units AF1 from poly-AF1.
  • Table 1 b List of the possible second chemical units AF2 or the possible components AF2 of poly-AF2.
  • the use of the poly-AF1 in combination with AF2 and / or poly-AF2 distinguishes the composition according to the invention functionally from molecules according to the prior art since the splitting of the functionalities on two non-chemically linked molecules, the two pi systems of AF1 and AF2 by twisting are not in conjugation, but are still fixed in close spatial proximity by the mixture in the inventive composition.
  • Known organic emitters usually consist of directly linked chemical units. Separation of the conjugated aromatic systems has not previously occurred, especially in conjunction with the localization of HOMO and LUMO on different compounds described herein.
  • the permissibility of a quantum mechanical transition is, as is well known, accessible either by theoretically derivable spectroscopic selection rules (symmetric molecules) or by measuring the extinction coefficient (UV / VIS spectroscopy) or quantum chemical calculation of the oscillator strength, with permission characterized by a large oscillator strength.
  • the greater the oscillator strength the faster the associated process.
  • saturation effects quickly occur at high current intensities, which adversely affects the component lifetime and prevents the achievement of high brightness levels.
  • a certain penetration of HOMO and LUMO is achieved by a mixture of a polymer with the functional motif of AF with another low or macromolecular AF (combined according to Table 2)
  • the quantum mechanical overlap integral increases the cooldown drops to values below 50 ps.
  • Oscillator strength can be determined by UVVIS spectroscopy, integrated with the lowest energy charge transfer band.
  • the combination of the chemical units poly-AF1 and poly-AF2 / AF2 results in correspondingly the exemplary compositions according to the invention of Table 2.
  • the unit AF1 has a structure of sub-formula 1a or has a structure of sub-formula 1a
  • VG3 bridging group is independently selected from the group consisting of each occurrence
  • Z is independently CR ** or N at each occurrence
  • R ** is independently at each occurrence either a radical R *, or a chemical bond to a spacer S, where exactly one R ** is a chemical bond to a spacer S.
  • the ring system formed from two or more of these substituents is limited to a monocyclic aliphatic ring system having a total of five or six ring members.
  • 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;
  • 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
  • R ** is independently at each occurrence either a radical R *, or a chemical bond to a spacer S, where exactly one R ** is a chemical bond to a spacer S.
  • R * is defined as in sub-formula 1 a.
  • 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
  • W is ⁇ or an element-element single bond, not two
  • Units W are simultaneously an element-element single bond, NR *, where not two units W are simultaneously NR *; R ** is independently at each occurrence either a radical R *, or a chemical bond to a spacer S, where exactly one R ** is a chemical bond to a spacer S.
  • R * is defined as in sub-formula 1 a.
  • the unit AF1 has a structure of sub-formula 1 .14 or has a structure of sub-formula 1.14
  • U is CR **, N, where a maximum of 3 units U are N at the same time, and no adjacent units U are 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 and dodecyl;
  • R ** is independently at each occurrence either a radical R *, or a chemical bond to a spacer S, where exactly one R ** is a chemical bond to a spacer S.
  • R * is defined as in sub-formula 1 a.
  • 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 independently selected from the group consisting of H, deuterium, alk, phenyl, pyridyl and CN, with a maximum of 4 units M are simultaneously CN, or denotes a chemical bond to a spacer S, exactly one M to a chemical bond a spacer S denotes.
  • 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 or S0 2 ;
  • D is N, CR *
  • T is N, CR **, with a maximum of 2 units T equal to N;
  • R ** is independently at each occurrence either a radical R *, or a chemical bond to a spacer S, where exactly one R ** is a chemical bond to a spacer S.
  • R * is defined as in sub-formula 1 a.
  • the unit AF1 has a structure of the sub-formulas 1 .25 to 1 .35 or has a structure of the sub-formulas 1.25 to 1.35
  • 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 spacer S, where exactly one R ** is a chemical bond is a spacer S and wherein the attachment to the spacer is made only via an R ** that is bound to a pure C-aromatic or C-ring.
  • R * is defined as in sub-formula 1 a.
  • unit AF2 has a structure of sub-formula 2 or has a structure of sub-formula 2
  • n 0, 1;
  • o 0, 1;
  • p 0, 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 **, R ** R ** , 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 at each occurrence a radical R * and / or marks a point of attachment to a spacer S, where exactly one R ** is a point of attachment to a spacer S.
  • R * is defined as in sub-formula 1 a.
  • the unit AF2 has a structure of the sub-formula 3 or has a structure of the sub-formula 3
  • 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.
  • the unit 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, sulfur; and, moreover, the definitions given for sub-formula 2 apply.
  • the chemical entity AF1 is selected from the group of the following structures:
  • # denotes the attachment positions to the spacer.
  • the chemical entity AF2 is selected from the group of the following structures: where:
  • # denotes the attachment positions to the spacer.
  • Table 2 Inventive combinations of AF1 and AF2, which meet the above-mentioned conditions of energy differences. Listed are the entries in the form AF number S (as placeholder) AF number. In brackets the values for AHOMO, ALUMO and Gap are given.
  • 70 - S- 64 (1.01 1.16 1.60)
  • 70 - S- 80 (0.92 1.01 1.75)
  • 70 - S- 81 (1.10 1.22 1.54)
  • 70 - S- 88 (1.09 1.73 1.02)
  • 77 - S- 1 13 (1.80 1.53 1.36)
  • 77 - S- 1 14 (1.97 0.93 1.96)
  • 77 - S- 1 18 (1.63 1.91 0.98)
  • 77 - S- 1 19 (1.91 1.79 1.10)
  • 77 - S-146 (1.68 1.52 1.37) 77 - S-147 (1.60 1.30 1.60) 77 - S-159 (1.41 0.86 2.03) 77 - S-164 (1.34 1.28 1.61)
  • 77 - S-273 (1.23 1.12 1.77)
  • 77 - S-274 (1.20 1.34 1.55)
  • 77 - S-277 (1.21 1.10 1.79)
  • 77 - S-278 (1.51 0.99 1.91)
  • 77 - S-305 (1.31 0.97 1.92)
  • 77 - S-306 (1.08 1.14 1.75)
  • 77 - S-308 (1.26 1.21 1.68)
  • 77 - S-309 (1.25 1.15 1.74)
  • 101 - s - 34 (0.801.641.38) 101 - s - 59 (0.891.721.30) 101 - s - 60 (1.301.581.44) 101 - s - 64 (1,121,531.50)
  • HO-S-17 (2.62 1.98 1.23) HO-S-19 (2.44 1.48 1.74) HO S-20 (1.58 0.82 2.40) HO S-26 (2.16 1.1 1 2.10)
  • HO-S-40 (1.58 1.38 1.84) HO-S-47 (1.08 1.67 1.55) HO S-49 (1.12 2.1 1 1.10) HO S-60 (1.76 2.23 0.98)
  • HOS-164 (1.021.281.93) HOS-160 (1.231.321.89) HOS-168 (0.82 1.33 1.88) HOS-175 (1.031.681.53)
  • HOS-181 (1.911.641.57) HOS-197 (0.831.991.23) HOS-198 (1.77 1.87 1.34) HOS-199 (1.421.391.82)
  • HO-S-210 (0.950.822.39) HO-S-211 (1.130.892.33) HO-S-212 (1.00 1.12 2.10) HO-S-213 (1.101.441.78)
  • HOS-215 (1.622.300.92) HOS-227 (1.070.912.30) HOS-228 (0.81 0.99 2.23) HOS-237 (1.701.661.55)
  • HO-S-244 (0.931.112.11) HO-S-246 (1.101.571.64) HO-S-247 (1.1 1 1.37 1.85) HO-S-250 (1.552.151.06)
  • HOS-253 (0.960.852.36) HOS-254 (1.010.932.28) HOS-255 (1.36 1.27 1.94) HOS-258 (1.081.581.64)
  • HO-S-259 (1,121,781.43) HO-S-260 (0.841.261.95) HO-S-265 (0.96 1.10 2.1 1) HO-S-270 (0.801.261.96)
  • HOS-273 (0.901.122.09) HOS-274 (0.881.341.87) HOS-277 (0.89 1.10 2.12) HOS-278 (1.180.992.23)
  • HO-S-279 (1.211.611.60) HO-S-280 (2.352.021.19) HO-S-281 (1.69 1.68 1.54) HO-S-282 (1.191.491.73)
  • HOS-283 (1,641,521.70)
  • HOS-284 (1,401,761.45)
  • HOS-285 (1.68, 1.76, 1.46)
  • HOS-286 (0,990,892.32)
  • HO-S-287 (1.441.251.96)
  • HO-S-288 (1.131.202.02)
  • HO-S-289 (0.88 1.29 1.92)
  • HO-S-290 (1.051.431.79)
  • HOS-294 (1.732.081.13) HOS-295 (1.452.221.00) HOS-300 (1.16 0.82 2.39) HOS-301 (1.571.421.79)
  • HO-S-303 (1.051.212.00) HO-S-305 (0.990.972.24) HO-S-308 (0.94 1.21 2.01) HO-S-309 (0.921.152.07)
  • 140 - S- 16 (1.40 1.13 2.27)
  • 140 - S- 17 (1.43 0.98 2.43)
  • 140 - S- 50 (1.07 2.21 1.19)
  • 140 - S- 89 (1.07 1.16 2.24)
  • 140 - S - 117 (0.83 1.77 1.64)
  • 140 - S - 144 (0.81 1.08 2.33)
  • 140 - S - 280 (1.15 1.02 2.39)
  • 141 - S - 50 (0.93 1.39 1.33)
  • 155- S- 13 (2.52 1.43 1.51)
  • 155- S- 14 (1.70 0.87 2.07)
  • 155- S- 15 (3.07 1.99 0.95)
  • 155- S- 16 (2.42 1.69 1.25)
  • 155- S-281 (1.51 1.23 1.71)
  • 155- S-282 (1.02 1.04 1.90)
  • 155- S-283 (1.47 1.07 1.87)
  • 155- S-284 (1.22 1.31 1.63)

Landscapes

  • Chemical & Material Sciences (AREA)
  • Health & Medical Sciences (AREA)
  • Organic Chemistry (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Emergency Medicine (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

L'invention concerne une composition homogène à base de molécules et de polymères purement organiques (colorants), qui ne comportent pas d'atomes métalliques et peuvent être utilisés en tant qu'émetteurs dans des composants optoélectroniques. Une telle composition comprend un polymère poly-AF1, un autre composant AF2 ou poly-AF2, de faible masse moléculaire ou de type macromoléculaire, et éventuellement un autre composant H ou de type macromoléculaire, ayant des propriétés hôte et éventuellement un autre composant M de faible poids moléculaire ou de type macromoléculaire.
PCT/EP2016/051172 2015-01-20 2016-01-20 Compositions s'utilisant en particulier dans des composants optoélectroniques WO2016116530A1 (fr)

Priority Applications (1)

Application Number Priority Date Filing Date Title
DE112016000391.9T DE112016000391A5 (de) 2015-01-20 2016-01-20 Zusammensetzungen, insbesondere zur Verwendung in optoelektronischen Bauelementen

Applications Claiming Priority (4)

Application Number Priority Date Filing Date Title
EP15151870.1 2015-01-20
EP15151870 2015-01-20
EP15168295.2 2015-05-20
EP15168295 2015-05-20

Publications (1)

Publication Number Publication Date
WO2016116530A1 true WO2016116530A1 (fr) 2016-07-28

Family

ID=55273217

Family Applications (1)

Application Number Title Priority Date Filing Date
PCT/EP2016/051172 WO2016116530A1 (fr) 2015-01-20 2016-01-20 Compositions s'utilisant en particulier dans des composants optoélectroniques

Country Status (2)

Country Link
DE (1) DE112016000391A5 (fr)
WO (1) WO2016116530A1 (fr)

Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20010015432A1 (en) * 2000-02-10 2001-08-23 Tatsuya Igarashi Light emitting device material comprising iridium complex and light emitting device using same material
EP1281745A1 (fr) * 2001-07-30 2003-02-05 Sumitomo Chemical Company, Limited Substance fluorescente polymerique et dispositif electroluminescent organique l'utilisant
EP1424350A1 (fr) * 2001-08-31 2004-06-02 Nippon Hoso Kyokai Compose phosphorescent, composition phosphorescente et element luminescent organique
WO2012013271A1 (fr) * 2010-07-30 2012-02-02 Merck Patent Gmbh Dispositif électroluminescent organique

Patent Citations (4)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US20010015432A1 (en) * 2000-02-10 2001-08-23 Tatsuya Igarashi Light emitting device material comprising iridium complex and light emitting device using same material
EP1281745A1 (fr) * 2001-07-30 2003-02-05 Sumitomo Chemical Company, Limited Substance fluorescente polymerique et dispositif electroluminescent organique l'utilisant
EP1424350A1 (fr) * 2001-08-31 2004-06-02 Nippon Hoso Kyokai Compose phosphorescent, composition phosphorescente et element luminescent organique
WO2012013271A1 (fr) * 2010-07-30 2012-02-02 Merck Patent Gmbh Dispositif électroluminescent organique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
LAMANSKY S ET AL: "MOLECULARLY DOPED POLYMER LIGHT EMITTING DIODES UTILIZING PHOSPHORESCENT PT(II) AND IR(III) DOPANTS", ORGANIC ELECTRONICS, ELSEVIER, AMSTERDAM, NL, vol. 2, no. 1, 1 March 2001 (2001-03-01), pages 53 - 62, XP001100541, ISSN: 1566-1199, DOI: 10.1016/S1566-1199(01)00007-6 *

Also Published As

Publication number Publication date
DE112016000391A5 (de) 2017-10-05

Similar Documents

Publication Publication Date Title
EP3247770B1 (fr) Molécules organiques destinées en particulier à être utilisées dans des composants optoélectroniques
EP1675930B1 (fr) Nouveaux materiaux pour l'electroluminescence et leur utilisation
WO2016116525A1 (fr) Molécules organiques, notamment pour une utilisation dans des composants opto-électroniques
EP3247769A1 (fr) Molécules organiques substituées par un éther phénylique, en particulier pour une utilisation dans des composants optoélectroniques
EP2009014A1 (fr) Utilisation d'un précurseur d'un n-dopant destiné au dopage d'un matériau semi-conducteur organique, précurseur et composant électronique ou optoélectronique
DE10349033A1 (de) Neue Materialien für die Elektrolumineszenz und deren Verwendung
EP3538623A1 (fr) Composés pourvus d'un groupe accepteur et d'un groupe donneur
EP3247765B1 (fr) Azoles à utiliser dans des composants optoélectroniques
EP3230404B1 (fr) Matériaux hôtes ambipolaires et leur utilisation
EP3247771B1 (fr) Pyridines et leurs dérivés en tant que constituants utilisables dans des composants optoélectroniques
EP3585777B1 (fr) Molécules organiques, en particulier destinées à être utilisées dans des dispositifs optoélectroniques organiques
WO2016116504A1 (fr) Molécules organiques à utiliser dans des composants optoélectroniques
DE102016113277A1 (de) Organische Moleküle zur Verwendung in optoelektronischen Bauelementen
EP3247766A1 (fr) Molécules organiques à utiliser dans des composants optoélectroniques
DE10330761A1 (de) Mischungen von organischen zur Emission befähigten Halbleitern und Matrixmaterialien, deren Verwendung und Elektronikbauteile enthaltend dieses
WO2016116508A1 (fr) Molécules organiques à utiliser en particulier dans des composants optoélectroniques
WO2016116524A2 (fr) Molécules organiques à utiliser dans des composants optoélectroniques
DE102010046412B4 (de) Metall-Ligand Koordinationsverbindungen
WO2018024723A1 (fr) Composés comprenant du phtalimide et du carbazol ou leurs analogues, trouvant application dans des dispositifs optoélectroniques
WO2016116530A1 (fr) Compositions s'utilisant en particulier dans des composants optoélectroniques
WO2016116522A1 (fr) Molécules organiques à utiliser dans des composants optoélectroniques
WO2018024725A1 (fr) Molécules organiques trouvant application dans des dispositifs optoélectroniques organiques
DE102015108002A1 (de) Zusammensetzung zur Verwendung in optoelektronischen Bauelementen
WO2016116527A1 (fr) Molécules organiques notamment utilisées dans des composants optoélectroniques
WO2017158083A1 (fr) Molécules organiques pour une utilisation en tant qu'émetteurs

Legal Events

Date Code Title Description
121 Ep: the epo has been informed by wipo that ep was designated in this application

Ref document number: 16702351

Country of ref document: EP

Kind code of ref document: A1

WWE Wipo information: entry into national phase

Ref document number: 112016000391

Country of ref document: DE

REG Reference to national code

Ref country code: DE

Ref legal event code: R225

Ref document number: 112016000391

Country of ref document: DE

122 Ep: pct application non-entry in european phase

Ref document number: 16702351

Country of ref document: EP

Kind code of ref document: A1