WO2010112799A1 - Luminophores comprenant des complexes platine-ligands - Google Patents

Luminophores comprenant des complexes platine-ligands Download PDF

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Publication number
WO2010112799A1
WO2010112799A1 PCT/GB2010/000349 GB2010000349W WO2010112799A1 WO 2010112799 A1 WO2010112799 A1 WO 2010112799A1 GB 2010000349 W GB2010000349 W GB 2010000349W WO 2010112799 A1 WO2010112799 A1 WO 2010112799A1
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Prior art keywords
ligand
platinum
complex
bidentate
complex according
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PCT/GB2010/000349
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English (en)
Inventor
Duncan W. Bruce
Valery N. Kozhevnikov
Amedeo Santoro
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University Of York
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Priority claimed from GB0903271A external-priority patent/GB0903271D0/en
Priority claimed from GB0903279A external-priority patent/GB0903279D0/en
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Publication of WO2010112799A1 publication Critical patent/WO2010112799A1/fr

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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07F—ACYCLIC, CARBOCYCLIC OR HETEROCYCLIC COMPOUNDS CONTAINING ELEMENTS OTHER THAN CARBON, HYDROGEN, HALOGEN, OXYGEN, NITROGEN, SULFUR, SELENIUM OR TELLURIUM
    • C07F15/00—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System
    • C07F15/0006—Compounds containing elements of Groups 8, 9, 10 or 18 of the Periodic System compounds of the platinum group
    • C07F15/0086—Platinum compounds
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/06—Non-steroidal liquid crystal compounds
    • C09K19/34—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring
    • C09K19/3441—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom
    • C09K19/3444—Non-steroidal liquid crystal compounds containing at least one heterocyclic ring having nitrogen as hetero atom the heterocyclic ring being a six-membered aromatic ring containing one nitrogen atom, e.g. pyridine
    • 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
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K19/40—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit containing elements other than carbon, hydrogen, halogen, oxygen, nitrogen or sulfur, e.g. silicon, metals
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/30—Coordination compounds
    • H10K85/341—Transition metal complexes, e.g. Ru(II)polypyridine complexes
    • H10K85/346—Transition metal complexes, e.g. Ru(II)polypyridine complexes comprising platinum
    • 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
    • C09K19/00—Liquid crystal materials
    • C09K19/04—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit
    • C09K2019/0425—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a specific unit that results in a functional effect
    • C09K2019/0433—Liquid crystal materials characterised by the chemical structure of the liquid crystal components, e.g. by a specific unit characterized by a specific unit that results in a functional effect the specific unit being a luminescent or electroluminescent unit
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K2101/00—Properties of the organic materials covered by group H10K85/00
    • H10K2101/10—Triplet emission
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K50/00—Organic light-emitting devices
    • H10K50/10—OLEDs or polymer light-emitting diodes [PLED]
    • H10K50/11—OLEDs or polymer light-emitting diodes [PLED] characterised by the electroluminescent [EL] layers

Definitions

  • the present invention relates to novel metal complexes with application as the emissive component in organic light emitting diodes, methods of their preparation and their use. More particularly, the invention relates to novel liquid crystals which are also light emitting materials. Thus, the invention also relates to materials comprising such liquid crystals and the use of such materials in, for example, display devices and light sources.
  • OLEDs Organic Light-Emitting Diodes
  • OLEDs are widely used in a new generation of low-power, flat-panel (and flexible) displays and are being examined for their use as lighting sources.
  • advantages offered by OLEDs is the possibility for preparation of very flexible displays and lighting sources in novel formats such as conformable panels or coatings for textiles and also the fact that backlighting is not required, so reducing energy consumption.
  • metal-organic luminophores that emit from triplet states are based on, for example:
  • liquid crystals have long range structural order, existing in so-called mesophases.
  • An attractive and central feature of liquid crystal mesophases is that the organisation of the molecules therein results in attendant anisotropy of the physical properties. It is because of these anisotropic properties that liquid crystals (and to some extent "liquid crystal like” materials) are versatile and responsive materials, which form the basis of the current flat- panel display industry and are the dominant technology in the market place.
  • metal complex OLED displays are likely to be energy efficient when compared to existing technology, incorporating long range order and anisotropic properties into molecules used to make metal-organic OLED displays may make a significant further increase in their energy efficiency.
  • various prior art documents disclose polycyclic liquid crystals, such as, DE4427199 which discloses 3,4-difluoro pyridine derivatives; JP2003286319 which discloses optically active fumaric acid diester derivatives as liquid crystals; JPl 1092451 which discloses phenyl pyrimidine derivatives, such as, 2 (3-fiuoro-4- hexyloxyphenyl)-5-(4-((S)-2-fluoro-2- methyldecanoyloxy)phenyl)pyrimidine; EP0739884 which discloses biphenyl pyrimidines; US5,550,236 which discloses polycyclic phenylene, pyrazine, pyridazine and pyrimidine compounds and fluorinated analogues; US6,171,519 which discloses thiadiazole derivatives; US5,443,752 which discloses various polycyclic liquid crystals; US5,447,656 which discloses various polycyclic
  • the present invention is based on the discovery of novel materials which are luminescent and more particularly materials which combine the properties of both liquid crystals and luminescence, e.g. phosphorescent, metal-organic complexes.
  • the present invention is based on the discovery of novel materials which combine the properties of both liquid crystals and metal-organic OLEDs.
  • a platinum-ligand complex comprising at least two types of ligands one of which comprises a bidentate donor ligand wherein the complex has accessible triplet states and a molecular structure that confers nematic and smectic phase liquid-crystal like properties.
  • liquid crystals are due to the ability of liquid crystal molecules to align.
  • molecules other than liquid crystals can be brought to alignment and therefore by the term "liquid crystal like” we mean molecules that can be so brought to alignment. This shall include liquid crystals, but shall not be limited thereto.
  • the complex may include at least two different types of ligands.
  • a first ligand will generally be a bidentate donor ligand.
  • bidentate donor ligands will include, inter alia, those bidentate ligands known from the prior art and hereinbefore described and which are incorporated herein by reference.
  • a ligand will comprise a bidentate C-N donor ligand.
  • An especially preferred C-N donor ligand is based on a 2,5- diphenylpyridine moiety, for example of the general formula I
  • n and m which may be the same or different, are each an integer from 1 to 30;
  • X 1 and X 2 which may be the same or different, are each -O- or a bond; and R 1 and R 2 are each hydrogen or R 1 and R 2 together form a 5- or 6-membered carbocyclic ring or a heterocyclic ring.
  • the second ligand may be selected from the group consisting of one or more of a diketone, such as an alkyl Cl to 10 or haloalkyl Cl to 10 diketone, a sulphoxide, such as a dialkyl Cl to 10 sulphoxide, and halogen, such as chlorine.
  • a diketone such as an alkyl Cl to 10 or haloalkyl Cl to 10 diketone
  • a sulphoxide such as a dialkyl Cl to 10 sulphoxide
  • halogen such as chlorine.
  • the di- ⁇ -chloro complexes which may lead subsequently to emissive complexes including dimethyl sulphoxide (DMSO), carbon monoxide (CO) a bidentate O ⁇ O donor ligand, such as a diketone, e.g., acetylacetonate (acac) and ⁇ - hydroxyketones, e.g.
  • DMSO dimethyl
  • a bidentate N-O donor ligand such as a, pyridine carboxylate, e.g. 2-picolinate or a fused-ring pyridine such as 8-hydroxyquinolate.
  • the second ligand is selected from the group consisting of one or more of halogen, dimethyl sulphoxide (DMSO), carbon monoxide (CO), a bidentate O ⁇ O donor ligand, or a bidentate N-O donor ligand.
  • a platinum-ligand complex wherein the second ligand is a bidentate 0-0 donor ligand may be desirable.
  • an especially preferred second ligand comprises a 1,3-diketone moiety of the general formula II
  • R 1 ⁇ and R ⁇ which may be the same or different, are each alkyl Cl to 10, preferably Cl to 6, or haloalkyl Cl to 10, preferably Cl to 6, such as trifluoromethyl, and isomers thereof.
  • platinum complex of the invention may be represented by a complex of formula X;
  • R x 1 and R x 2 together; and R x 3 and R x 4 together, each form an optionally substituted and optionally fused carbocyclic ring or heterocyclic ring; and R x 5 and R x 6 , which may be the same or different are each a ligand selected from the group consisting of halogen, such as -Cl, -S O(CHa) 2 or CO; or R x 5 and R x 6 may together form a bidentate O ⁇ O donor ligand, or a bidentate N-O donor ligand, as hereinbefore described.
  • carrier means a saturated, unsaturated or aromatic, ring system containing 6 to 14 ring carbon atoms, which may be unsubstituted or substituted as defined and as described herein or as a known polycyclic liquid crystal as hereinbefore described.
  • heterocyclic ring as used herein means an optionally substituted, saturated or unsaturated non-aromatic 4-, 5-, 6-, or 7-membered ring that contains at least one heteroatom selected from O, S and N.
  • platinum complex of the invention may be represented by a complex of formula XI;
  • R 1 , R 2 , X 1 , X 2 , R x 5 , R x 6 , m and n are each as hereinbefore defined.
  • R 1 and R 2 together form a 5- or 6-membered carbocyclic ring and especially a saturated carbocyclic ring.
  • R x 5 and R x 6 together form a bidentate O ⁇ O donor ligand, such as, a diketone ligand, e.g. derived from a compound of formula II as hereinbefore described.
  • R 1 and R 2 together form a 5- or 6-membered carbocyclic ring, especially a 5-membered carbocyclic ring, and R x 5 and R x 6 together form a diketone ligand, e.g. derived from a compound of formula II.
  • Certain of the compounds of formula I are known, for example, those in which R 1 and R 2 are hydrogen. However, certain compounds of formula I are novel per se, for example, those in which R 1 and R 2 together form a 5- or 6-membered carbocyclic ring.
  • Ligands and complexes of the invention and intermediates may be prepared by methods generally known per se or other process schemes which may be utilised which include those set out below:
  • a material comprising a platinum- ligand complex with accessible triplet states and a molecular structure that confers liquid-crystal like properties on the material as hereinbefore described.
  • a material is advantageous in that, inter alia, it is a luminophore and may also be a liquid crystal.
  • the material as hereinbefore described in the manufacture of an electronic device.
  • the material is advantageous in that, inter alia, such electronic devices or light sources may be more energy-efficient and/or brighter than conventionally known devices or may emit polarised light. It is within the scope of the present invention to provide a material comprising the organo-platinum luminophore as hereinbefore described in combination with one or more known liquid crystals.
  • Figure 1 illustrates the molecular structure of the two, independent molecules in the unit cell of 8-6;
  • Figure 2 illustrates the molecular structure of the complex 12-6;
  • Figure 3 illustrates the molecular structure of the complex 17-6A;
  • Figure 4 illustrates the arrangement of one pair of complexes: 17-6B and 17-6C;
  • Figure 5 illustrates optical micrographs (on cooling) of the (a) SmC phase at 203 °C; (b) the SmI phase at 198°C; (c) SmF phase at 159°C; (d) crystal smectic G phase at 152 0 C;
  • Figure 6 is a plot of the clearing point as a function of compound for ligands 1-n and 2-n and complexes 8- « and 12- «;
  • Figure 9 is the normalized emission spectra of thin films of 8-12 in polycarbonate at the proportions by mass indicated; the spectrum of the neat film after heating to 110°C is also shown;
  • Figure 10 is the normalized emission spectra of thin films of 12-12 in polycarbonate at the proportions by mass indicated, together with the spectrum of the neat film after heating to 110°C;
  • 2,5-Di(4-methoxyphenyl)pyridine (3.60 mmol, 1.05 g) was added to molten pyridinium chloride (45.43 mmol, 5.25 g) at 200°C and stirred for 16 h. After some cooling, the still warm mixture was added to water (50 cm 3 ) and stirred for 15 minutes. The resulting solid was recovered by filtration and washed with water (100 cm 3 ) and propanone (100 cm 3 ), to give a green solid. Yield 0.56 g (2.14 mmol, 59%)
  • 2,5-Di(4-methoxyphenyl)cyclopentenopyridine (3.59 mmol, 1,19 g)was added to molten pyridinium chloride (45.43 mmol, 5.25 g) at 200 0 C and stirred for 12 h.
  • water (50 cm 3 ) was added and the mixture stirred for 15 minutes.
  • the solid was recovered by filtration and washed with water (100 cm 3 ) and propanone (100 cm 3 ), to give a dark solid. Yield 0.98 g (3.23 mmol, 90%).
  • 2,5-Di(4-hydroxyphenyl)-cyclopentenopyridine (1.90 mmol, 0.581 g) was added to a solution of 1-bromododecane (4.73 mmol, 1.18 g) and potassium carbonate (5.50 mmol, 0.762 g) in DMF (20 cm 3 ). The solution was stirred and heated at 90°C for 12 hours. After the mixture was cooled, it was dissolved in water (150 cm 3 ), filtered off the precipitate and washed with ethanol (50 cm 3 ) and propanone (25 cm 3 ).
  • Complex 8-12 Complex 11-12 (0.110 mmol, 0.100 g) was added to a solution of sodium acetylacetonate monohydrate (1.16 mmol, 0.163 g) in propanone (60 cm 3 ), and stirred at room temperature for 4 h. After the reaction the solvent was removed by rotary evaporator, washed with water (50 cm 3 ), and crystallized from propanone.
  • Complex 12-12 (0.11 mmol, 0.100 g) was added to a solution of sodium acetylacetonate monohydrate (0.23 mmol, 0.032 g) in propanone (60 cm 3 ), and stirred at room temperature for 12 h. After the reaction the solvent was removed by rotary evaporator, the product was solubilised in CH 2 Cl 2 and then filtered. The solvent was removed by rotary evaporator and the crude product was purified by short column chromatography on silica, using chloroform as eluant. Yield 0.086 g (0.93 mmol, 85%).
  • the structure determinations served to confirm the predicted structure of the complexes.
  • the only point of note is perhaps that in complex 12-6, the pyridine ring is modified by having a fused cyclopentene ring attached which causes the twisting out of plane of the unbound phenyl ring attached to the pyridine. This may account for the blue shift in the emission wavelength of complexes 8 compared to 12.
  • the higher energy of the emissive state of 12-12 is likely to arise from the steric influence of the ortho-C ⁇ i groups of the cyclopentene ring in disfavouring the planar structure that would maximize conjugation between the rings.
  • Ic 1 and ⁇ k m are the radiative and non-radiative rate constants estimated on the basis of the luminescence quantum yield and lifetime, (b) Bimolecular rate constant of quenching by molecular oxygen, estimated from lifetimes in degassed and aerated solutions, (c) In ether- isopentane-ethanol (2:2:1). (d) In 2-methyltetrahydrofuran; data from reference.
  • the complexes are very brightly luminescent, with emission lifetimes at room temperature of 27 ⁇ s.
  • the quantum yields at room temperature are around 0.70 - considerably superior to that of [Pt(ppy)(acac)]. Indeed the values are competitive with the brightest Pt-based emitters, and appear to be the highest hitherto reported for platinum with ppy-based ligands.
  • the luminescence of complexes 8-12 and 12-12 was studied at several concentrations within a polycarbonate (PC) host, as thin films prepared by spin coating.
  • PC polycarbonate
  • the emission spectrum is unchanged on increasing the concentration from 1% to 50%, but higher concentrations result in a small increase in the relative intensity of the red component of the emission. Normalized spectra are shown in Fig. 9.
  • This enhanced, low-energy emission may be due to the formation of aggregates or excimers, a feature frequently encountered for square planar platinum(II) complexes which can undergo intermolecular face-to-face interactions, for example, through overlap of the d z 2 andp z orbitals orthogonal to the plane of the molecule.
  • TM'TM For example, such species have been used recently to produce white light by extending the emission across the visible region.”
  • a similar effect is observed for the cyclopentene-appended complex 12-12 at high doping levels in PC (Fig. 10).

Abstract

L'invention concerne des complexes platine-ligands comportant au moins deux types de ligands dont un comprend un donneur, lesdits complexes ayant des états de triplets accessibles et des structures moléculaires conférant des propriétés semblables aux phases nématiques et smectiques des cristaux liquides. La figure illustre les spectres d'émission de 2 composés selon la présente demande en solution dans du dichlorométhane à 198 K (λβχ = 400 nm) conjointement avec ceux de[Pt(ppy)(acac)] à titre de comparaison.
PCT/GB2010/000349 2009-02-26 2010-02-26 Luminophores comprenant des complexes platine-ligands WO2010112799A1 (fr)

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GB0903271A GB0903271D0 (en) 2009-02-26 2009-02-26 Luminophores
GB0903271.5 2009-02-26
GB0903279.8 2009-02-27
GB0903279A GB0903279D0 (en) 2009-02-27 2009-02-27 Luminophores

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Cited By (8)

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Publication number Priority date Publication date Assignee Title
WO2011114095A1 (fr) * 2010-03-13 2011-09-22 University Of York Luminophores
DE102010054893A1 (de) * 2010-12-17 2012-06-21 Osram Opto Semiconductors Gmbh Strahlungsemittierende organisch-elektronische Vorrichtung und Verfahren zu deren Herstellung
WO2012121189A1 (fr) * 2011-03-10 2012-09-13 国立大学法人九州大学 Matériau phosphorescent, procédé de production d'un matériau phosphorescent et élément phosphorescent
WO2014034384A1 (fr) * 2012-08-31 2014-03-06 国立大学法人九州大学 Matériau luminescent organique, procédé pour produire le matériau luminescent organique, et élément luminescent organique
CN104245674A (zh) * 2012-04-17 2014-12-24 霍夫曼-拉罗奇有限公司 新苯基-四氢异喹啉衍生物
WO2016014983A1 (fr) * 2014-07-24 2016-01-28 Universal Display Corporation Dispositif oled à couche(s) d'amélioration
CN108586369A (zh) * 2018-05-30 2018-09-28 中国科学院长春应用化学研究所 苯基三嗪化合物的制备方法及苯基吡啶化合物的制备方法
CN111187300A (zh) * 2020-01-10 2020-05-22 常州大学 基于环金属铂配合物手性液晶磷光材料的构筑及其在圆偏振器件中的应用

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WO2011114095A1 (fr) * 2010-03-13 2011-09-22 University Of York Luminophores
DE102010054893A1 (de) * 2010-12-17 2012-06-21 Osram Opto Semiconductors Gmbh Strahlungsemittierende organisch-elektronische Vorrichtung und Verfahren zu deren Herstellung
US9735397B2 (en) 2010-12-17 2017-08-15 Osram Oled Gmbh Radiation-emitting organic-electronic device and method for the production thereof
CN103732719B (zh) * 2011-03-10 2015-12-02 国立大学法人九州大学 磷光发光材料、磷光发光材料的制造方法以及磷光发光元件
WO2012121189A1 (fr) * 2011-03-10 2012-09-13 国立大学法人九州大学 Matériau phosphorescent, procédé de production d'un matériau phosphorescent et élément phosphorescent
JP5128728B1 (ja) * 2011-03-10 2013-01-23 国立大学法人九州大学 リン光発光材料、リン光発光材料の製造方法、及びリン光発光素子
CN103732719A (zh) * 2011-03-10 2014-04-16 国立大学法人九州大学 磷光发光材料、磷光发光材料的制造方法以及磷光发光元件
TWI472594B (zh) * 2011-03-10 2015-02-11 Univ Kyushu 磷光發光材料、磷光發光材料之製造方法及磷光發光元件
CN104245674B (zh) * 2012-04-17 2017-07-11 霍夫曼-拉罗奇有限公司 苯基‑四氢异喹啉衍生物
CN104245674A (zh) * 2012-04-17 2014-12-24 霍夫曼-拉罗奇有限公司 新苯基-四氢异喹啉衍生物
JP5625140B2 (ja) * 2012-08-31 2014-11-12 国立大学法人九州大学 有機発光材料、有機発光材料の製造方法、及び有機発光素子
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