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WO1993014177A1 - Polymere conjugue - Google Patents

Polymere conjugue Download PDF

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Publication number
WO1993014177A1
WO1993014177A1 PCT/GB1993/000131 GB9300131W WO9314177A1 WO 1993014177 A1 WO1993014177 A1 WO 1993014177A1 GB 9300131 W GB9300131 W GB 9300131W WO 9314177 A1 WO9314177 A1 WO 9314177A1
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WO
WIPO (PCT)
Prior art keywords
polymer
leaving group
poly
conjugated
process according
Prior art date
Application number
PCT/GB1993/000131
Other languages
English (en)
Inventor
Donal Donat Conor Bradley
Paul Leslie Burn
Richard Henry Friend
David Alan Halliday
Andrew Bruce Holmes
Arno Kraft
Original Assignee
Cambridge Display Technology Limited
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 Cambridge Display Technology Limited filed Critical Cambridge Display Technology Limited
Publication of WO1993014177A1 publication Critical patent/WO1993014177A1/fr

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Classifications

    • H—ELECTRICITY
    • H01—ELECTRIC ELEMENTS
    • H01B—CABLES; CONDUCTORS; INSULATORS; SELECTION OF MATERIALS FOR THEIR CONDUCTIVE, INSULATING OR DIELECTRIC PROPERTIES
    • H01B1/00—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors
    • H01B1/06—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances
    • H01B1/12—Conductors or conductive bodies characterised by the conductive materials; Selection of materials as conductors mainly consisting of other non-metallic substances organic substances
    • H01B1/124—Intrinsically conductive polymers
    • H01B1/128—Intrinsically conductive polymers comprising six-membered aromatic rings in the main chain, e.g. polyanilines, polyphenylenes
    • 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
    • C08F8/00—Chemical modification by after-treatment
    • C08F8/44—Preparation of metal salts or ammonium salts
    • C—CHEMISTRY; METALLURGY
    • C08—ORGANIC MACROMOLECULAR COMPOUNDS; THEIR PREPARATION OR CHEMICAL WORKING-UP; COMPOSITIONS BASED THEREON
    • C08G—MACROMOLECULAR COMPOUNDS OBTAINED OTHERWISE THAN BY REACTIONS ONLY INVOLVING UNSATURATED CARBON-TO-CARBON BONDS
    • C08G61/00—Macromolecular compounds obtained by reactions forming a carbon-to-carbon link in the main chain of the macromolecule
    • C—CHEMISTRY; METALLURGY
    • C09—DYES; PAINTS; POLISHES; NATURAL RESINS; ADHESIVES; COMPOSITIONS NOT OTHERWISE PROVIDED FOR; APPLICATIONS OF MATERIALS NOT OTHERWISE PROVIDED FOR
    • C09K—MATERIALS FOR MISCELLANEOUS APPLICATIONS, NOT PROVIDED FOR ELSEWHERE
    • C09K11/00—Luminescent, e.g. electroluminescent, chemiluminescent materials
    • C09K11/06—Luminescent, e.g. electroluminescent, chemiluminescent materials containing organic luminescent materials
    • H—ELECTRICITY
    • H05—ELECTRIC TECHNIQUES NOT OTHERWISE PROVIDED FOR
    • H05B—ELECTRIC HEATING; ELECTRIC LIGHT SOURCES NOT OTHERWISE PROVIDED FOR; CIRCUIT ARRANGEMENTS FOR ELECTRIC LIGHT SOURCES, IN GENERAL
    • H05B33/00—Electroluminescent light sources
    • H05B33/12—Light sources with substantially two-dimensional radiating surfaces
    • H05B33/14—Light sources with substantially two-dimensional radiating surfaces characterised by the chemical or physical composition or the arrangement of the electroluminescent material, or by the simultaneous addition of the electroluminescent material in or onto the light source

Definitions

  • the present invention relates to conjugated polymers, more particularly to conjugated poly(arylenevinylene) polymers having improved electronic properties.
  • the present invention also relates to methods of making the polymers.
  • Conjugated polymers are of considerable interest for applications as electronically or optically active materials because they can combine the ease and cheapness of processing of a processible polymer together with the semiconducting or conducting properties usually associated with inorganic materials. Processing of these polymers, usually to form a thin film, is conveniently performed from solution by such methods as spin or dip coating, or from a melt. Although the conjugated polymer itself may commonly be insoluble in convenient solvents or infusible below its decomposition temperature, methods are available to overcome this problem.
  • the method of Lenz et al describes how poly(p-phenylenevinylene) , PPV, an intractable polymer, can be prepared via a solution-processible "precursor" polymer formed as a sulphonium polyelectrolyte (R.W. Lenz, C-C Han, J. Stenger-Smith, and F.E. Karasz in Journal of Polymer Science: Part A: Polymer Chemistry 1988, 26_, 3241).
  • PPV produced by this method is shown in Figure 1 as PPV(a),or via a methoxy leaving group precursor polymer (S. Tokito, T. Momii, H. Murata, T. Tsutsui and S.
  • the sulphonium polyelectrolyte (shown as [1] in Figure 1) is soluble in both water and methanol and it is possible to obtain films of high quality from a solution in methanol. These films have been used as the emissive layer in large-area light-emitting diodes as discussed in International Patent Application No. W090/13148 of the present applicant.
  • Another strategy to achieve a soluble polymer is to attach flexible side-groups to the main chain and this has been achieved for PPV with attachment of alkoxy groups to the 2 and 5 positions on the phenylene ring.
  • poly(2,5-dihexyloxy- phenylene vinylene) as disclosed in S.H. Askari, S.D. Rughooputh and F. Wudl, Synthetic Metals 1989, .29., E129.
  • Both of these methods for the preparation of the conjugated polymer suffer from the disadvantage that the soluble phase is likely to be one in which the polymer is disordered. Where the polymer is in the form of a random coil in solution, it is difficult to remove this disorder in the conjugated form of the polymer once it has been converted. Electronic and optical properties are very sensitive to the presence of defects, including conformational defects on the polymer chain.
  • the present invention provides a conjugated polymer which is preparable from a solution-processible precursor polymer and which exhibits in optical absorption spectroscopy its greatest amplitude of absorption at the photon energy equal to that of the (0,0) electronic transition across the semiconductor energy-gap in comparison to that at the energies of any of the vibronic side-bands of the (0,0) electronic transition.
  • a conjugated poly(arylenevinylene) polymer is also provided which exhibits in optical absorption spectroscopy its greatest amplitude of absorption at the photon energy equal to that of the (0,0) electronic transition across the semiconductor energy-gap in comparison to that at the energies of any of the vibronic side-bands of the (0,0) electronic transition.
  • the conjugated poly(arylenevinylene) polymer is preparable from a solution-processible precursor polymer.
  • arylene is intended to include in its scope all types of arylenes including heteroarylenes as well as arylenes incorporating more than one ring structure, including fused ring structures.
  • the poly(arylenevinylene) polymer is a poly(phenylenevinylene) polymer which may be substituted or unsubstituted.
  • a preferred example of the poly(phenylene- vinylene) polymer is poly(p-phenylenevinylene) , PPV. - A -
  • an important characteristic of the electronic structure of the conjugated polymer of the present invention is provided by the spectrally-resolved optical absorption and photoluminescence.
  • a sharp onset is observed at around 2.4 eV and a peak in absorption at about 2.45 eV.
  • the absorption spectrum shows a series of subsidiary peaks or shoulders. These are assigned to optical transitions that couple to the vibrational quanta for the polymer chain.
  • the luminescent spectra are complementary, showing a peak in emission just below the absorption edge and subsidiary maxima at lower energies, again spaced by the vibrational quanta for the polymer chain.
  • the peak in emission is at about 2.35 eV.
  • the conjugated polymer of the present invention has a greater absorption amplitude in the (0,0) transition than in any of the other vibronic side-bands.
  • the conjugated polymers of the present invention appear to have a high level of chain order in comparison with polymers found in the prior art. This is discussed in further detail below.
  • the present invention also provides a process for preparing a conjugated polymer, which process comprises providing a leaving group substituted precursor polymer comprising saturated and unsaturated units, the saturated units of which include a leaving group, reacting the leaving group substituted precursor polymer in a solvent comprising a modifier group at a temperature whereby the modifier group substitutes some or all of the leaving groups leaving groups, and converting the solution-processible precursor polymer to the conjugated polymer under conditions to eliminate the modifier group, wherein the solvent and temperature are selected such that the conjugated polymer produced exhibits in optical absorption spectroscopy its greatest amplitude of absorption at the photon energy equal to that of the (0,0) electronic transition across the semiconductor energy-gap in comparison to that at the energies of any of the vibronic side-bands of the (0,0) electronic transition.
  • the precursor polymer has introduced in its structure a sufficient amount of unsaturation to minimise the amount of disorder within the polymer chain.
  • Standard spectroscopic techniques may be used to characterise the precursor polymers. It has been found that a typical proportion of unsaturated units in the precursor polymer should be up to 40%. If too much unsaturation is introduced the precursor polymer may cease to be solution processible and precipitate from solution.
  • the modifier group present in the precursor polymer must be capable of elimination from the precursor polymer so as to yield an unsaturated unit typically conjugated with further unsaturated units in the polymer.
  • the conditions of elimination must be such that the polymer is not decomposed.
  • an uncharged modifier group is used such as a methoxy group, although charged modifier groups such as sulphonium moieties may be used.
  • the solution-processible precursor polymer is selected so that it may be converted into one of the conjugated polymers as described above.
  • the solution-processible precursor polymer comprises a poly(arylenevinylene) polymer
  • a proportion of the vinylic groups of the polymer are typically substituted with the modifier group.
  • Standard conditions of elimination may be employed, such as heating in the presence of acid substantially in the absence of oxygen.
  • an inert gas atmosphere is used.
  • the solution-processible polymer is provided by reacting a leaving group substituted precursor polymer, advantageously in a solvent comprising the modifier group so that the modifier group replaces the leaving group, so as to form the solution-processible precursor polymer.
  • a preferred solvent is methanol whereby a methoxy modifier group is provided directly as the solvent.
  • the leaving group substituted precursor polymer is preferably provided in a different solvent from that comprising the modifier group and may be formed by any suitable reaction of monomer units.
  • conversion of the leaving group substituted precursor polymer into the solution-processible precursor polymer takes place with an increase in the proportion of unsaturated units present in the polymer. Control of the degree of unsaturation in the solution-processible precursor polymer may be achieved by appropriate variation of the time and temperature for reaction. Where a methoxy modifier group is used, the preferred reaction temperature is over 50 C, more preferably around 55 C.
  • an initial precursor polymer is formed.
  • This initial precursor polymer is then reacted in solution in the presence of base so as to form the leaving group substituted precursor polymer.
  • the reaction conditions can be tailored so as further to control the degree of unsaturation in the leaving group substituted precursor polymer.
  • leaving group substituted precursor polymers may be formed having an appropriate degree of unsaturation for subsequent formation into the solution-processible precursor polymer.
  • a preferred base for this reaction is an organic base, typically one which is soluble in organic solvents.
  • a tetra alkylammonium hydroxide base is used such as tetra-n-butylammonium hydroxide.
  • tetra-n-butylammonium hydroxide an amount of less than one molar equivalent is preferred so as to prevent conversion into an insoluble product.
  • the leaving group present in the solution-processible and leaving group substituted precursor polymers is a sulphonium leaving group.
  • the polymers of the present invention may be exploited in many applications including electroluminescent devices.
  • the energy of the peak emission is blue-shifted. This enables some control of colour of emission in comparison with conventional PPV.
  • the ranges of wavelengths for the electroluminescence emissions is narrowed so that a greater fraction of the emitted light falls within a given colour range.
  • Figure 1 shows the various synthetic routes for forming PPV both as described in the prior art and in the present invention
  • Figure 2 shows optical absorption spectra measured at room temperature for the PPVs (a) to (i) of Figure 1;
  • Figure 3 shows the photoluminescence spectra at 10K for selected PPVs
  • Figures 4 to 12 shows the infra-red spectra of each of the PPVs (a) to (i);
  • Figures 13 to 16 show respectively the infra-red spectra of precursor polymers ([4], [9], [10], and [11] of Figure- 1) ;
  • Figure 17 shows the UV/visible spectra of the precursor polymers ([4], [9], [10], and [11] of Figure 1).
  • De-oxygenated aqueous sodium hydroxide (0.4 M, 29.5 ml) was added dropwise to a stirred, deoxygenated ice cold solution of l,l'-[l,4-phenylenebis(methylene)]bis[tetrahydrothiophenium] dichloride [2](4.00g, 11.8 mmol) in methanol (30ml). The reaction mixture was stirred for 1 hour and then neutralised with dilute hydrochloric acid.
  • the product was then dialysed against distilled water (3 x 1000 ml) at room temperature, under argon for 3 days, using a cellulose membrane dialysis tubing with molecular weight cut-off of 12400 (supplied by Sigma Chemical Company Limited, Dorset, U.K.), the dialysis medium being changed every 24 hours.
  • the solvent was completely removed from the material in the dialysis tubing and the polymer residue [1] was redissolved in dry methanol. Films of [1] were obtained by spin-coating or free casting and then thermally converted (220°C, 12 hours, under vacuum) to give films of PPV(a) .
  • films were spin-coated onto spectrosil substrates from either methanol or chloroform solutions, and were converted by heat treatment at 220 C for 12 hours, under flowing Ar with HCl.
  • the product was then dialysed against methanol (3 x 1000 ml) at room temperature under argon for 3 days, using a cellulose membrane dialysis tubing with molecular weight cut-off of 12400 (supplied by Sigma Chemical Company Limited, Dorset, U.K.), the dialysis medium being changed every 24 hours.
  • a solution of polymer [3] in methanol (11 mg/ml, 120 ml) was prepared and the solution was divided into 6 aliquots.
  • the absorption spectra for the improved PPVs; PPV(f), PPV(g) , PPV(h) and PPV(i) show a sharp onset at around 2.4 eV and a peak in absorption a little below 2.5 eV.
  • the absorption spectra shows a series of subsidiary peaks, or shoulders, and these are assigned to optical transitions that couple to the vibrational quanta for the chain.
  • the luminescence spectra are complementary, showing the peak in emission just below the absorption edge, and subsidiary maxima at lower energies, again spaced by the vibrational quanta for the chain.
  • the peaks in absorption and emission at 2.45 and 2.35 eV are identified respectively, as the transitions between the vibrational ground states of the electronic ground and excited states, termed the (0,0) transitions.
  • the effect of disorder in the polymer is to broaden the absorption and emission features, and also to shift oscillator strength away from the (0,0) transitions, that is, to higher energy for absorption and to lower energy for emission.
  • the spectra obtained for the improved PPV are readily distinguished from those seen for previous forms of PPV.
  • Polymers with the high level of chain order seen here can be quantitatively differentiated from those with more normal levels of order through the relative strengths of the vibronic side-bands seen in the emission and absorption spectra.
  • the material made here is identified as having a greater absorption amplitude at the photon energy equal to that of the (0,0) transition than at the energies of any of the other vibronic side-bands.
  • oxidising agents such as sulphuric acid and iodine
  • reducing agents such as sodium or potassium.
  • Another method for introducing carriers is to form a field-effect device such as a Metal-Insulator-Semiconductor Field Effect Transistor, in which carriers are introduced through formation of space or surface charge layers. Another method is through optical absorption across the energy gap to produce separated electron-hole pairs.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Spectroscopy & Molecular Physics (AREA)
  • Physics & Mathematics (AREA)
  • General Chemical & Material Sciences (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Electroluminescent Light Sources (AREA)

Abstract

Polymère conjugué qu'on peut préparer à partir d'un polymère de précurseur pouvant être traité par solution, et dont la plus grande amplitude d'absorption au niveau de l'énergie photonique, en spectroscopie d'absorption optique, est égale à celle de la transition électronique (0,0) au niveau de la longueur de bande interdite du semiconducteur si on la compare aux energies de n'importe laquelle des bandes latérales vibroniques de la transition électronique (0,0). L'invention concerne également un polymère de poly(arylènevinylène) conjugué tel que du poly(p-phénylènevinylène). Ce polymère conjugué peut être utilisé dans diverses applications dans lesquelles une structure électronique améliorée est utile, comme c'est le cas dans les dispositifs électroluminescents.
PCT/GB1993/000131 1992-01-21 1993-01-21 Polymere conjugue WO1993014177A1 (fr)

Applications Claiming Priority (2)

Application Number Priority Date Filing Date Title
GB9201240.0 1992-01-21
GB929201240A GB9201240D0 (en) 1992-01-21 1992-01-21 Conjugated polymer

Publications (1)

Publication Number Publication Date
WO1993014177A1 true WO1993014177A1 (fr) 1993-07-22

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WO (1) WO1993014177A1 (fr)

Cited By (10)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0700235A1 (fr) * 1994-08-29 1996-03-06 Hoechst Aktiengesellschaft Procédé de structuration de films polymères de polyarylènevinylène par irradiation de lumière
WO1996010617A1 (fr) * 1994-09-30 1996-04-11 Hoechst Aktiengesellschaft Derives de poly(paraphenylene-vinylene) et leur utilisation comme materiaux electroluminescents
WO1996020253A1 (fr) * 1994-12-28 1996-07-04 Cambridge Display Technology Ltd. Polymeres destines a des dispositifs optiques
WO1998004610A1 (fr) * 1996-07-29 1998-02-05 Cambridge Display Technology Limited Copolymeres conjugues prevus pour etre utilises dans des dispositifs luminescents
WO1998013408A1 (fr) * 1996-09-28 1998-04-02 Cambridge Display Technology Limited Copolymeres hautement efficaces
WO1998032783A1 (fr) * 1997-01-28 1998-07-30 Cambridge Display Technology Ltd. Modification de la rheologie de solutions precurseurs
US5807974A (en) * 1996-05-16 1998-09-15 Korea Institute Of Science And Technology Fluorene-based alternating copolymers for electroluminescence element and electroluminescence element using such copolymers as light emitting materials
US6559256B2 (en) 1994-12-28 2003-05-06 Cambridge Display Technology Ltd. Polymers for use in optical devices
US6949291B2 (en) 2000-09-26 2005-09-27 Cambridge Display Technology Limited Twisted polymers, uses thereof and processes for the preparation of statistical copolymers
US8377570B2 (en) 2004-11-01 2013-02-19 Agency For Science, Technology And Research Poly(arylenevinylene) and poly(heteroarylenevinylene) light emitting polymer and polymer light-emitting devices

Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4528118A (en) * 1983-04-28 1985-07-09 Agency Of Industrial Science And Technology Highly electroconductive conjugated polymer composition and process for producing the same
WO1990013148A1 (fr) * 1989-04-20 1990-11-01 Cambridge Research And Innovation Limited Dispositifs electroluminescents
EP0443861B1 (fr) * 1990-02-23 1995-07-05 Sumitomo Chemical Company Limited Dispositif électroluminescent organique

Patent Citations (3)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
US4528118A (en) * 1983-04-28 1985-07-09 Agency Of Industrial Science And Technology Highly electroconductive conjugated polymer composition and process for producing the same
WO1990013148A1 (fr) * 1989-04-20 1990-11-01 Cambridge Research And Innovation Limited Dispositifs electroluminescents
EP0443861B1 (fr) * 1990-02-23 1995-07-05 Sumitomo Chemical Company Limited Dispositif électroluminescent organique

Non-Patent Citations (1)

* Cited by examiner, † Cited by third party
Title
JOURNAL OF MOLECULAR ELECTRONICS vol. 4, no. 1, 1988, CHICHESTER pages 44 - 45 H.FRIEND 'optical investigations of conjugated polymers' *

Cited By (23)

* Cited by examiner, † Cited by third party
Publication number Priority date Publication date Assignee Title
EP0700235A1 (fr) * 1994-08-29 1996-03-06 Hoechst Aktiengesellschaft Procédé de structuration de films polymères de polyarylènevinylène par irradiation de lumière
US6361917B1 (en) 1994-08-29 2002-03-26 Hoechst Aktiengesellschaft Process for patterning poly(arylenevinylene) polymer films by irradiation with light
WO1996010617A1 (fr) * 1994-09-30 1996-04-11 Hoechst Aktiengesellschaft Derives de poly(paraphenylene-vinylene) et leur utilisation comme materiaux electroluminescents
CN1066163C (zh) * 1994-09-30 2001-05-23 赫彻斯特股份公司 用作电致发光材料的含氮聚合物
EP1006169A1 (fr) * 1994-12-28 2000-06-07 Cambridge Display Technology Limited Polymères destinés à des dispositifs optiques
US7795802B2 (en) 1994-12-28 2010-09-14 Cambridge Display Technology Ltd. Polymers for use in optical devices
US6919415B2 (en) 1994-12-28 2005-07-19 Cambridge Display Technology Ltd. Polymers for use in optical devices
US7365141B2 (en) 1994-12-28 2008-04-29 Cambridge Display Technology Ltd. Polymers for use in optical devices
US7105621B2 (en) 1994-12-28 2006-09-12 Cambridge Display Technology Ltd. Polymers for use in optical devices
WO1996020253A1 (fr) * 1994-12-28 1996-07-04 Cambridge Display Technology Ltd. Polymeres destines a des dispositifs optiques
EP1291406A1 (fr) * 1994-12-28 2003-03-12 Cambridge Display Technology Limited Polymères destinés à des dispositifs optiques
US6559256B2 (en) 1994-12-28 2003-05-06 Cambridge Display Technology Ltd. Polymers for use in optical devices
US6723811B1 (en) 1994-12-28 2004-04-20 Cambridge Display Technology Ltd. Polymers for use in optical device
US5807974A (en) * 1996-05-16 1998-09-15 Korea Institute Of Science And Technology Fluorene-based alternating copolymers for electroluminescence element and electroluminescence element using such copolymers as light emitting materials
WO1998004610A1 (fr) * 1996-07-29 1998-02-05 Cambridge Display Technology Limited Copolymeres conjugues prevus pour etre utilises dans des dispositifs luminescents
US6423428B1 (en) 1996-07-29 2002-07-23 Cambridge Display Technology Limited Conjugated copolymers for use in luminescent devices
WO1998013408A1 (fr) * 1996-09-28 1998-04-02 Cambridge Display Technology Limited Copolymeres hautement efficaces
WO1998032783A1 (fr) * 1997-01-28 1998-07-30 Cambridge Display Technology Ltd. Modification de la rheologie de solutions precurseurs
US6153711A (en) * 1997-01-28 2000-11-28 Cambridge Display Technology Ltd. Rheology modification of precursor solutions
GB2335430B (en) * 1997-01-28 2000-09-13 Cambridge Display Tech Ltd Rheology modification of precursor solutions
GB2335430A (en) * 1997-01-28 1999-09-22 Cambridge Display Tech Ltd Rheology modification of precursor solutions
US6949291B2 (en) 2000-09-26 2005-09-27 Cambridge Display Technology Limited Twisted polymers, uses thereof and processes for the preparation of statistical copolymers
US8377570B2 (en) 2004-11-01 2013-02-19 Agency For Science, Technology And Research Poly(arylenevinylene) and poly(heteroarylenevinylene) light emitting polymer and polymer light-emitting devices

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Publication number Publication date
AU3361793A (en) 1993-08-03
GB9201240D0 (en) 1992-03-11

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