US20030186079A1 - Luminescent polymer - Google Patents

Luminescent polymer Download PDF

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US20030186079A1
US20030186079A1 US10/169,692 US16969202A US2003186079A1 US 20030186079 A1 US20030186079 A1 US 20030186079A1 US 16969202 A US16969202 A US 16969202A US 2003186079 A1 US2003186079 A1 US 2003186079A1
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polymer according
polymer
light
optical device
triarylene
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Carl Towns
Richard O'Dell
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Cambridge Display Technology Ltd
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Priority claimed from GBGB0000091.9A external-priority patent/GB0000091D0/en
Priority claimed from GBGB0004542.7A external-priority patent/GB0004542D0/en
Priority claimed from PCT/GB2000/000911 external-priority patent/WO2000055927A1/en
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Assigned to CAMBRIDGE DISPLAY TECHNOLOGY LIMITED reassignment CAMBRIDGE DISPLAY TECHNOLOGY LIMITED ASSIGNMENT OF ASSIGNORS INTEREST (SEE DOCUMENT FOR DETAILS). Assignors: O'DELL, RICHARD, TOWNS, CARL
Publication of US20030186079A1 publication Critical patent/US20030186079A1/en
Assigned to IPIFS GUARANTEE CORP. reassignment IPIFS GUARANTEE CORP. CONDITIONAL ASSIGNMENT Assignors: CAMBRIDGE DISPLAY TECHNOLOGY LIMITED
Assigned to CAMBRIDGE DISPLAY TECHNOLOGY LIMITED reassignment CAMBRIDGE DISPLAY TECHNOLOGY LIMITED CANCELLATION OF CONDITIONAL ASSIGNMENT Assignors: IPIFS GUARANTEE CORP.
Priority to US11/872,216 priority Critical patent/US8361636B2/en
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Definitions

  • the present invention relates to a novel luminescent polymer, especially for use in an optical device such as an optical device comprising an electroluminescent device.
  • Electroluminescent devices are structures which emit light when subject to an applied electric field.
  • an electroluminescent device comprises a light-emissive layer between two electrodes.
  • the cathode electrode injects negative charge carriers (electrons) and the anode electrode injects positive charge carriers (holes) into the light-emissive layer.
  • Light emission occurs when the electrons and holes combine in the light-emissive layer to generate photons.
  • one of the electrodes is typically transparent, to allow the photons to escape the device.
  • the light-emissive layer should be made from a light-emissive material which may be laid down as a film without substantially affecting the luminescent characteristics of the material and which is stable at the operational temperature of the device.
  • Organic electroluminescent devices which use an organic material as the light-emissive material are known in this art.
  • organic materials simple aromatic molecules such as anthracene, perylene and coronene are known to show electroluminescence.
  • U.S. Pat. No. 4,539,507 discloses the use of small molecule organic materials as the light-emissive material, such as 8-hydroxy quinoline(aluminium)“Alq”.
  • PCT/WO90/13148 discloses an electroluminescent device comprising a semiconducting layer comprising a polymer film as the light-emissive layer which comprises at least one conjugated polymer.
  • the polymer film comprises a poly(para-phenylenevinylene)(PPV) film.
  • the colour of the light generated by the light-emissive material is determined by the optical gap or bandgap of the organic light-emissive materials, that is to say the difference in energy levels between the “highest occupied molecular orbital” (“HOMO”) and the “lowest unoccupied molecular orbital” (“LUMO”) levels.
  • the bandgap is the energy difference between the valence and conduction bands.
  • the semiconductive conjugated copolymer comprises at least two chemically different monomer units which, when existing in their individual homopolymer forms, typically have different semiconductor bandgaps.
  • the proportion of the chemically different monomer units in the copolymer can be selected to control the semiconductor bandgap of the copolymer so as to control the optical properties of the copolymer.
  • the extent of conjugation of the copolymer can be said to affect the ⁇ - ⁇ * bandgap of the copolymer. Increasing the extent of conjugation has the effect of decreasing the bandgap up to the point of bandgap convergence.
  • EP 0686662 discloses a device for emitting green light.
  • the anode is a layer of transparent indium-tin oxide.
  • the cathode is a LiAl layer.
  • Between the electrodes is a light-emissive layer of PPV.
  • the device comprises also a hole transport layer of polyethylene dioxythiophene which provides an intermediate energy level which aids the holes injected from the anode to reach the HOMO level in the PPV.
  • polymers made by electrochemical oxidative coupling usually are not suitable for use as emitters in an electroluminescent device. This is because they have poor device characteristics such as having a large number of defects and being substantially insoluble and not processable.
  • Narrow bandgap systems symbolised as ⁇ A-Q-A ⁇ n , where A is a kind of aromatic-donor unit and Q is a kind of o-quinoid-acceptor unit are disclosed in “Design of Narrow-bandgap polymers”, Chem. Mater., 1996, 8, pages 570-578.
  • the bandgaps determined from the polymers on ITO-coated glass electrodes vary from 0.5 to 1.4 eV. The authors conclude that these values are small compared with usual conjugated polymers, confirming that the polymers are narrow-band gap systems. Furthermore, the authors conclude that the results show that the bandgap is widely tuneable by the polymer structure.
  • red light means wavelengths in the range of 595 to 800 nm, preferably 595 to 700 nm, preferably 610 to 650 nm, especially around 630 nm and especially wavelengths having a peak around 650 to 660 nm.
  • the present invention provides a luminescent polymer comprising a triarylene repeat unit which comprises a triarylene of general formula I which is substituted or unsubstituted and an arylene repeat unit ⁇ Ar ⁇ that is different from the triarylene repeat unit:
  • X, Y and Z are each independently a group VI element or an alkyl-or aryl-substituted group V or group IV element.
  • the polymer comprising a triarylene repeat unit which is an unsubstituted triarylene of formula:
  • the present polymer comprises repeat units of the general formula II:
  • the molar ratio of triarylene repeat unit: Ar is particularly advantageous for the molar ratio of triarylene repeat unit: Ar to be up to approximately 1:1.
  • the percent by weight triarylene could be in the range 0.1-50%, preferably in the range 5-10%.
  • the present polymer comprises repeat units of the general formula III:
  • the triarylene repeat unit comprises the general formula IV:
  • R 1 to R 6 comprises an alkyl, aryl, heteroaryl, alkylaryl, arylalkyl, CN or halide substituent.
  • the aryl, heteroaryl, alkylaryl or arylalkyl is phenyl, heterophenyl, alkylphenyl or phenylalkyl.
  • R 1 to R 6 are H.
  • substituent R groups may be chosen so as to enhance solubility, efficiency and/or effect the colour of emission by steric or electronic effects.
  • R 3 and/or R 4 are methyl.
  • R 1 ,R 2 ,R 3 ,R 4 ,R 5 and R 6 are all H.
  • R 1 and/or R 6 comprise an alkyl, aryl, CN or halide while R 2 ,R 3 ,R 4 and R 5 are all H. More preferably, R 1 and R 6 each comprise hexyl and R 2 ,R 3 ,R 4 and R 5 are all H. This is because the applicants have found that substitution at positions R 2 , R 3 , R 4 or R 5 leads to a twisting of the triarylene unit. In turn, this reduces ⁇ -conjugation and, therefore, increases the bandgap. This would seem to be due to steric hindrance. Electronic effects also may play a role in this effect.
  • X, Y and Z are each independently O, S, C, Si or N, more preferably, O or S. Still more preferably X, Y and Z all are S. Again, it has been found that these groups result in coplanar conformations of the polymer which maximises ⁇ -conjugation.
  • a further preferred embodiment may be where X and Z are O and Y is S.
  • arylene repeat units ⁇ Ar ⁇ which are useful in the present polymer may advantageously comprise a 2,7-linked 9,9 dialkyl fluorene, a 2,7-linked 9,9 diaryl fluorene, a p-linked dialkyl phenylene, a p-linked dialkoxy phenylene, a phenylene vinylene, a 2,5-linked benzothiadiazole, a 2,5-linked alkyl benzothiadiazole, a 2,5-linked dialkyl benzothiadiazole, a 2,5-linked substituted or unsubstituted thiophene, a triarylamine or a bis triarylamine.
  • ⁇ Ar ⁇ may be other substituted or unsubstituted aromatic systems such as polycyclic aromatics, fused aromatics or heterocycles.
  • the polymer further comprises a further repeat unit of general formula V:
  • repeat unit is substituted or unsubstituted, wherein Q is O, S, CR 2 , SiR 2 or NR, more preferably O or S, still more preferably S.
  • the degree of polymerisation of the present polymer must be sufficient to achieve bandgap convergence.
  • Bandgap convergence means the band gap obtained where any further increase in effective conjugation does not affect the band gap.
  • the degree of polymerisation is preferably at least 4.
  • each variable in the present polymer should be chosen so that the polymer is capable of emitting light at a wavelength in the range 600 to 690 nm
  • the variables are chosen also so as to make the polymer soluble. This has the advantage of allowing the polymer to be processed in solution.
  • the present polymer may be prepared by a number of methods.
  • a preferred method of preparation is described in U.S. Pat. No. 5,777,070.
  • the process involves contacting (i) monomers having two reactive groups selected from boronic acid, C 1 -C 6 boronic acid ester, C 1 -C 6 borane and combinations thereof with aromatic dihalide functional monomers or (ii) monomers having one reactive boronic acid, boronic acid ester or borane group and 1 reactive halide functional group with each other.
  • aromatic monomers are proposed including those containing triarylamines.
  • the polymerisation reaction product of this process has conjugated unsaturated internal groups.
  • Polymers according to the present invention which have been produced by this method are particularly advantageous. This is because reaction times are short and residual catalyst e.g. palladium levels are low.
  • the present invention further provides a composition comprising a mixture comprising a luminescent polymer according to this invention.
  • the composition comprises a luminescent polymer comprising a triarylene repeat unit which is an unsubstituted triarylene of formula:
  • composition may be in any suitable form, for example laid down as a sheet or layer.
  • the present polymer may be used in an optical device such as an optical device comprising an electroluminescent device.
  • Such devices may comprise a substrate and the present polymer supported on the substrate.
  • such electroluminescent devices would comprise a first charge carrier injecting layer for injecting positive charge carriers, a second charge carrier injecting layer for injecting negative charge carriers and a light-emissive layer located between the charge carrier injecting layers for accepting and combining positive and negative charge carriers to generate light.
  • the electroluminescent device may comprise a material for transporting negative charge carriers. This may either be located between the second charge carrier injecting layer and the light emissive-layer or may be located in the light-emissive layer. Where it is located in the light-emissive layer, it may be blended in a mixture with the light-emissive material.
  • the electroluminescent device may comprise a material for transporting positive charge carriers.
  • This either may be located between the first charge carrier injecting layer and the light-emissive layer or may be located in the light-emissive layer. Where it is located in the light-emissive layer, it may be blended in a mixture with the light-emissive material and optionally a material for transporting negative charge carriers.
  • One example of a blend or mixture which is particularly useful for use in the light-emissive layer of an electroluminescent device according to this invention consists of the three polymers shown below blended in a ratio of 99.6:0.2:0.2.
  • the light-emissive layer may consist only of this blend or may include further polymers. This blend is capable of emitting white light when excited to luminesce.
  • the polymer according to the present invention is used as a light-emissive material in the light-emissive layer of an electroluminescent device, advantageously, it may be blended in a mixture with a material for transporting negative charge carriers and/or a material for transporting positive charge carriers.
  • the polymer according to the present invention is capable of transporting positive and/or negative charge carriers when used in an electroluminescent device, it advantageously may be blended in a mixture with a light-emissive material in the light-emissive layer.
  • the polymer according to the present invention is blended in the light-emissive layer with one or more other materials, particularly one or more other polymers, the polymer according to the present invention preferably is present in the blend at a level of 0.2-30%, more preferably 0.5-30%.
  • the polymer according to the present invention preferably comprises a repeat unit as shown in Formula VI or VII below:
  • Example 1 The procedure outlined for Example 1 was followed using freshly distilled (0.045 mbar/89° C.) 2-(tributyl-stannyl) furan (7.2 mL, 22.8 mmol), dibromodimethyl benzothiadiazole (3.07 g, 9.53 mmol), and tetrakis (triphenylphosphine) palladium (0) (190 mg, 2 mol). After 18 h, the reaction was allowed to cool to room temp. and then the solvent was removed under vacuum.
  • alkyl substituents are provided for increased solubility.
  • the anode 2 is a layer of transparent indium-tin oxide (“ITO”) supported on a glass or plastic substrate 1 .
  • the anode 2 layer has a thickness between 1000-2000 ⁇ , usually about 1500 ⁇ .
  • the cathode 5 is a Ca layer having an approximate thickness of 1500 ⁇ .
  • Between the electrodes is a light emissive layer 4 having a thickness up to about 1000 ⁇ .
  • the emissive layer 4 comprises between 0.5 to 30% by weight of the present polymer with the remainder of the emissive layer consisting of hole and/or electron transport material.
  • the device includes a hole transport material layer 3 of PEDOT having a thickness of about 1000 ⁇ .
  • Layer 6 is an encapsulant layer of a suitable thickness.

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  • Chemical & Material Sciences (AREA)
  • Organic Chemistry (AREA)
  • Health & Medical Sciences (AREA)
  • Chemical Kinetics & Catalysis (AREA)
  • Medicinal Chemistry (AREA)
  • Polymers & Plastics (AREA)
  • Engineering & Computer Science (AREA)
  • Materials Engineering (AREA)
  • Polyoxymethylene Polymers And Polymers With Carbon-To-Carbon Bonds (AREA)
  • Electroluminescent Light Sources (AREA)
  • Addition Polymer Or Copolymer, Post-Treatments, Or Chemical Modifications (AREA)
  • Luminescent Compositions (AREA)
US10/169,692 2000-01-05 2001-01-04 Luminescent polymer Abandoned US20030186079A1 (en)

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GBGB0000091.9A GB0000091D0 (en) 2000-01-05 2000-01-05 Luminescent polymer
GB0004542.7 2000-02-25
GBGB0004542.7A GB0004542D0 (en) 2000-02-25 2000-02-25 Luminescent polymers
WOPCT/GB00/00911 2000-03-13
PCT/GB2000/000911 WO2000055927A1 (en) 1999-03-12 2000-03-13 Polymers, their preparation and uses
GB0000091.9 2000-05-01

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US20080233431A1 (en) * 2003-07-08 2008-09-25 Konica Minolta Holdings Inc. Organic electroluminescent element, illuminator and display
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US8642188B2 (en) * 2006-12-22 2014-02-04 Merck Patent Gmbh Phenanthroline compounds and electroluminescent devices using the same
US20100060152A1 (en) * 2006-12-22 2010-03-11 Merck Patent Gmbh Phenanthroline compounds and electroluminescent devices using the same
US20100108993A1 (en) * 2007-02-01 2010-05-06 Sumitomo Chemical Company, Limited Block copolymer and polymer light-emitting device
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US20130090446A1 (en) * 2010-06-23 2013-04-11 Mingjie Zhou Polymer containing units of fluorene, anthracene and benzothiadiazole, preparation method thereof and application thereof
JP2013534949A (ja) * 2010-06-23 2013-09-09 オーシャンズ キング ライティング サイエンス アンド テクノロジー シーオー．，エルティーディー フルオレン、アントラセン及びベンゾチアジアゾール単位を含むポリマー、その調製方法及びその使用
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US20140135460A1 (en) * 2011-11-21 2014-05-15 Gwangju Institute Of Science And Technology Low band gap copolymer and method for manufacturing same
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US9184392B2 (en) * 2012-02-06 2015-11-10 Lg Chem, Ltd. Polymer and organic solar cell including same
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US11031557B2 (en) 2014-10-22 2021-06-08 Raynergy Tek Inc. Conjugated polymers based on terthiophene and their applications

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CN1404521A (zh) 2003-03-19
WO2001049768A2 (en) 2001-07-12
DE60107380T2 (de) 2005-12-01
CN1252215C (zh) 2006-04-19
US8361636B2 (en) 2013-01-29
AU2690001A (en) 2001-07-16
JP2003519266A (ja) 2003-06-17
US20080053520A1 (en) 2008-03-06
EP1244723A2 (de) 2002-10-02
DE60107380D1 (de) 2004-12-30
WO2001049768A3 (en) 2002-01-03
EP1244723B1 (de) 2004-11-24

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