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• • H—ELECTRICITY
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/649—Aromatic compounds comprising a hetero atom
  • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
  • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
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  • 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
  • H10K85/151—Copolymers
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D333/00—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom
  • C07D333/50—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems
  • C07D333/78—Heterocyclic compounds containing five-membered rings having one sulfur atom as the only ring hetero atom condensed with carbocyclic rings or ring systems condensed with rings other than six-membered or with ring systems containing such rings
• • C—CHEMISTRY; METALLURGY
  • C07—ORGANIC CHEMISTRY
  • C07D—HETEROCYCLIC COMPOUNDS
  • C07D495/00—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms
  • C07D495/02—Heterocyclic compounds containing in the condensed system at least one hetero ring having sulfur atoms as the only ring hetero atoms in which the condensed system contains two hetero rings
• • H—ELECTRICITY
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  • 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
  • H10K85/111—Organic polymers or oligomers comprising aromatic, heteroaromatic, or aryl chains, e.g. polyaniline, polyphenylene or polyphenylene vinylene
  • H10K85/113—Heteroaromatic compounds comprising sulfur or selene, e.g. polythiophene
• • 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
  • H10K85/20—Carbon compounds, e.g. carbon nanotubes or fullerenes
  • H10K85/211—Fullerenes, e.g. C60
  • H10K85/215—Fullerenes, e.g. C60 comprising substituents, e.g. PCBM
• • H—ELECTRICITY
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/615—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene
  • H10K85/626—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing more than one polycyclic condensed aromatic rings, e.g. bis-anthracene
• • H—ELECTRICITY
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  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/649—Aromatic compounds comprising a hetero atom
  • H10K85/655—Aromatic compounds comprising a hetero atom comprising only sulfur as heteroatom
• • 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
  • H10K85/60—Organic compounds having low molecular weight
  • H10K85/649—Aromatic compounds comprising a hetero atom
  • H10K85/657—Polycyclic condensed heteroaromatic hydrocarbons
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K30/00—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation
  • H10K30/30—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising bulk heterojunctions, e.g. interpenetrating networks of donor and acceptor material domains
• • H—ELECTRICITY
  • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
  • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
  • H10K39/00—Integrated devices, or assemblies of multiple devices, comprising at least one organic radiation-sensitive element covered by group H10K30/00
  • H10K39/30—Devices controlled by radiation
  • H10K39/32—Organic image sensors

Definitions

• the disclosure relates to photoactive compounds and their use in organic electronic devices, in particular organic photodetectors.
• organic electronic devices comprising organic semiconductor materials are known, including organic light-emitting devices, organic field effect transistors, organic photovoltaic (solar cell) devices and organic photodetectors (OPDs).
• organic light-emitting devices organic field effect transistors
• organic photovoltaic (solar cell) devices organic photodetectors (OPDs).
• OPDs organic photodetectors
• a drawback with OPDs is the presence of dark current, i.e. current flowing through the device in the absence of any photons incident on the device, which may affect the limit of detection of the device.
• dark current which is the term used for current flowing through the OPD in the absence of any photons being incident on the OPD, may affect the limit of photon detection of the OPD.
• OPD organic photovoltaics
• OPVs organic photovoltaics
• one key focus in the design of photodetectors is reducing the dark current.
• the specific detectivity may be increased.
• the dark current is decreased without compromising the responsivity and/or EQE of the device.
• solar cells often require a relatively broad spectral response at wavelengths where most of the sun irradiance lays (e.g. l ⁇ 900 nm).
• Photodetectors may operate in a specific or relatively narrow spectral band, which may be dependent upon a specific application.
• the OPDs described herein may be suitable for the detection of light in the NIR regions of the electromagnetic spectrum, where irradiance from the sun is depleted (e.g. > 900 or > 940 nm).
• the present inventors have found a class of acceptor compounds which may give low dark current as compared to the fullerene acceptor PCBM when used as an acceptor compound in an OPD.
• the inventors have surprisingly found that the acceptor compounds provide EQEs of greater than 40% across a wide spectrum of wavelengths when used as acceptor compounds in OPDs.
• this class of acceptor compounds may be suitable for detection of light in the near infra-red region, in particular wavelengths of about 900-1000 nm.
• OPDs comprising the acceptor compounds have been shown to exhibit an EQE that is greater than 40% at wavelengths of between about 900 nm and 950 nm.
• Sunlight is absorbed by atmospheric moisture at about 940 nm and so use of this class of acceptor compounds in a light source-OPD detector arrangement for detection of light having a wavelength in this range may be useable without shielding from sunlight. Because of absorption of sunlight in the atmosphere at these wavelengths, acceptor compounds according to the present disclosure may not be applicable to use in OPVs.
• an organic photodetector comprising an anode; a cathode; and a photosensitive organic layer between the anode and cathode, wherein the photosensitive organic layer comprises an electron donor material and an acceptor compound.
• the acceptor compound is a compound of formula (I):
• each R 11 and R 12 is independently selected from the group consisting of:
• R -R independently in each occurrence is selected from the group consisting of H, Ci_ 20 alkyl and an electron- withdrawing group; and each X is independently O, S, Se or Te.
• non-terminal C atom of an alkyl group as used herein is meant a carbon atom other than the methyl carbon atom of an n-alkyl group or the methyl carbon atoms of a branched alkyl group.
• electron-withdrawing group as used herein is meant a group having a positive para-substituent Hammett constant.
• exemplary groups with a positive para-substituent Hammett constant are halogens selected from F, Cl, Br, I or CN, N02, CF3 and Ci_i 2 fluoroalkyl.
• the present inventors have found that use of compounds of formula (I) may give improved uniformity of a photosensitive layer formed by a solution deposition method, as compared to a photosensitive layer containing a fullerene acceptor.
• an organic photodetector comprising formation of an organic photosensitive layer over one of an anode and cathode and formation of the other of the anode and cathode over the organic photosensitive layer, wherein formation of the organic photosensitive layer comprises deposition of a formulation comprising an electron donor material and an electron acceptor compound of formula (I) dissolved or dispersed in one or more solvents and evaporation of the one or more solvents.
• a sensor comprising a light source and an organic photodetector, wherein the organic photodetector is configured to receive light from the light source.
• a method of detecting light comprising measurement of a photocurrent generated by light incident on an organic photodetector.
• a use of a compound of formula (I) in a photosensitive layer of an organic photodetector comprising measurement of a photocurrent generated by light incident on an organic photodetector.
• Figure 1 illustrates an organic photodetector according to some embodiments
• Figure 2 is a graph of EQE vs wavelength for a device according to an embodiment and a comparative device
• Figure 3 is a graph of current density vs applied voltage in dark conditions for a device according to an embodiment and a comparative device.
• the words “comprise,” “comprising,” and the like are to be construed in an inclusive sense, as opposed to an exclusive or exhaustive sense; that is to say, in the sense of "including, but not limited to.”
• the terms “connected,” “coupled,” or any variant thereof means any connection or coupling, either direct or indirect, between two or more elements; the coupling or connection between the elements can be physical, logical, electromagnetic, or a combination thereof.
• the words “herein,” “above,” “below,” and words of similar import when used in this application, refer to this application as a whole and not to any particular portions of this application.
• words in the Detailed Description using the singular or plural number may also include the plural or singular number respectively.
• the word "or,” in reference to a list of two or more items, covers all of the following interpretations of the word: any of the items in the list, all of the items in the list, and any combination of the items in the list.
• FIG. 1 illustrates an OPD according to some embodiments of the present disclosure.
• the OPD comprises a cathode 103 supported by a substrate 101, an anode 107 and a bulk heterojunction layer 105 disposed between the anode and the cathode comprising a mixture of an electron acceptor and an electron donor.
• the bulk heterojunction layer consists of the electron acceptor and the electron donor.
• the OPD comprises a layer of material 106 which modifies the work function of the cathode 103. In other embodiments, this layer may or may not be present.
• the OPD may comprise other layers not shown in Figure 1.
• the device may comprise a hole transport layer (HTL) located between the anode 107 and the heterojunction layer 105.
• HTL hole transport layer
• the anode may be between the substrate and the bulk heterojunction layer and cathode.
• the photodetectors as described in this disclosure may be connected to a voltage source for applying a reverse bias to the device and a device configured to measure photocurrent.
• the photodetectors are part of a system comprising a plurality of photodetectors.
• the photodetectors may be part of an array in an image sensor of a camera.
• the voltage applied to the photodetector may be varied.
• the photodetector may be continuously biased when in use.
• a sensor may comprise a light source and an OPD as described herein wherein the OPD is configured to receive light emitted from the light source.
• the light from the light source may or may not be changed before reaching the light source.
• the light may be filtered, down-converted or up-converted before it reaches the light source.
• the sensor is configured to detect light having a wavelength in the range of about 900-1000 nm, optionally about 920-960 nm.
• acceptor compounds described herein are used in OPDs, they may be suitable for detection of longer wavelength applications, in particular wavelengths of greater than 900 nm.
• the electron acceptor compounds described herein do not comprise a fullerene group, and are described hereinafter as“non-fullerene acceptors”.
• An OPD comprising the acceptor compound may have an EQE of at least about 10%, 20%, 30%, 40%, 50%, 60%, 70%, 80% or 90% across a wide spectrum of wavelengths.
• the EQE is greater than about 40% at wavelengths of between about 350 nm and 950 nm.
• the EQE may be measured as for the device described in Example 1.
• an OPD comprising the non-fullerene acceptor as described herein, produces a dark current that is at least 10 times less than fullerene derivative CeoPCBM.
• the acceptor compound is a compound of formula (I)
• each R 11 and R 12 is independently selected from the group consisting of: - Ci-2o alkyl wherein one or more non-adjacent, non-terminal C atoms may be replaced with O, S, CO or COO; one or more H atoms may be replaced with F; and a terminal C atom may be replaced with Ar wherein Ar is an unsubstituted or substituted aromatic or heteroaromatic group; and - a group of formula (Ar 1 ⁇ wherein Ar 1 in each occurrence is independently an aromatic or heteroaromatic group which is unsubstituted or substituted with one or more substituents and n is at least 1; R 13 -R 16 independently in each occurrence is selected from the group consisting of H, F and Ci- 2 o alkyl wherein one or more non-adjacent, non-terminal C atoms may be replaced with O, S, CO or COO and one or more H atoms may be replaced with F;
• R -R independently in each occurrence is selected from the group consisting of H, Ci_ 20 alkyl and an electron- withdrawing group; and each X is independently O, S, Se or Te.
• Ar 1 may be a single ring or fused aromatic. Ar 1 may be selected from C 6-2 o aromatic groups and 5-20 membered heteroaromatic groups. In some preferred embodiments, Ar 1 is phenyl or thiophene, more preferably phenyl. n is preferably 1, 2 or 3, more preferably 1.
• Ar may be a single ring or fused aromatic. Ar may be selected from C 6-2 o aromatic groups and 5-20 membered heteroaromatic groups. In some preferred embodiments, Ar 1 is phenyl or thiophene, more preferably phenyl.
• Each Ar and Ar is independently unsubstituted or substituted with one or more substituents.
• Substituents of Ar 1 may be selected from substituents R 1 wherein R 1 in each occurrence is independently selected from F, CN, NO 2 and Ci_ 2 o alkyl wherein one or more non-adjacent, non-terminal C atoms may be replaced with O, S, CO or COO.
• C 1-20 alkyl is a preferred R 1 group.
• R and R are each a hydrocarbyl group.
• R 11 and R 12 independently in each occurrence are preferably selected from Ci_ 2 o alkyl, unsubstituted phenyl and phenyl substituted with one or more R 1 groups.
• R 13 in each occurrence is preferably selected from H, C 1-20 alkyl and C1-19 alkoxyl.
• one of two R groups bound to the same ring is H and the other R group is selected from Ci_ 2 o alkyl and C 1.19 alkoxyl.
• at least one R 14 is H.
• At least one R 15 is H.
• at least one R 16 is H.
• R -R independently is preferably H or F. In preferred embodiments, at least one or at least 2 of R 20 -R 23 is F.
• Each X is preferably S.
• the compound of formula (I) has a LUMO of 3.85 eV or deeper as measured by square wave voltammetry. By“deeper” as used herein is meant further from vacuum level.
• the compound of formula (I) has a HOMO-LUMO bandgap of less than 1.5 eV.
• Exemplary compounds of formula (I) are:
• the donor compound (p-type) is not particularly limited and may be appropriately selected from electron donating materials that are known to the person skilled in the art, including organic polymers, oligomers and small molecules.
• the donor compound can be a semiconducting polymer.
• the p-type donor compound comprises an organic conjugated polymer, which can be a homopolymer or copolymer including alternating, random or block copolymers. Preferred are non-crystalline or semi- crystalline conjugated organic polymers.
• the p-type organic semiconductor is a conjugated organic polymer with a low bandgap, typically between 2.5 eV and 1.5 eV, preferably between 2.3 eV and 1.8 eV.
• polymers selected from conjugated hydrocarbon or heterocyclic polymers including polyacene, polyaniline, polyazulene, polybenzofuran, polyfluorene, polyfuran, polyindenofluorene, polyindole, polyphenylene, polypyrazoline, polypyrene, polypyridazine, polypyridine, polytriarylamine, poly(phenylene vinylene), poly(3-substituted thiophene), poly(3,4- bisubstituted thiophene), polyselenophene, poly(3-substituted selenophene), poly(3,4- bisubstituted selenophene), poly(bisthiophene), poly(terthiophene), poly(bisselenophene), poly (ter selenophene), polythieno[2,3-b]thiophene, polythieno [3, 2-b] thiophene, polybenz
• Preferred examples of p-type donors are copolymers of polyfluorenes and polythiophenes, each of which may be substituted, and polymers comprising benzothiadiazole-based and thiophene-based repeating units, each of which may be substituted. It is understood that the p-type donor may also consist of a mixture of a plurality of electron donating materials.
• the weight of the donor compound to the acceptor compound is from about 1:0.5 to about 1:2.
• the weight ratio of the donor compound to the acceptor compound is about 1:1 or about 1:1.5.
• At least one of the first and second electrodes is transparent so that light incident on the device may reach the bulk heterojunction layer. In some embodiments, both of the first and second electrodes are transparent. Each transparent electrode preferably has a transmittance of at least 70%, optionally at least 80%, to wavelengths in the range of 300-900 nm.
• one electrode is transparent and the other electrode is reflective.
• the transparent electrode comprises or consists of a layer of transparent conducting oxide, preferably indium tin oxide or indium zinc oxide.
• the electrode may comprise poly 3,4-ethylenedioxythiophene (PEDOT).
• the electrode may comprise a mixture of PEDOT and polystyrene sulfonate (PSS).
• PSS polystyrene sulfonate
• the electrode may consist of a layer of PEDOT:PSS.
• the reflective electrode may comprise a layer of a reflective metal.
• the layer of reflective material may be aluminium or silver or gold.
• a bi-layer electrode may be used.
• the electrode may be an indium tin oxide (ITO)/silver bi-layer, an ITO/aluminium bi-layer or an ITO/gold bi-layer.
• the device may be formed by forming the bulk heterojunction layer over one of the anode and cathode supported by a substrate and depositing the other of the anode or cathode over the bulk heterojunction layer.
• the area of the OPD may be less than about 3 cm , less than about 2 cm , less than about 1 cm 2 , less than about 0.75 cm 2 , less than about 0.5 cm 2 or less than about
• the substrate may be, without limitation, a glass or plastic substrate.
• the substrate can be described as an inorganic semiconductor.
• the substrate may be silicon.
• the substrate can be a wafer of silicon.
• the substrate is transparent if, in use, incident light is to be transmitted through the substrate and the electrode supported by the substrate.
• the substrate supporting one of the anode and cathode may or may not be transparent if, in use, incident light is to be transmitted through the other of the anode and cathode.
• the bulk heterojunction layer may be formed by any process including, without limitation, thermal evaporation and solution deposition methods.
• the bulk heterojunction layer is formed by depositing a formulation comprising the acceptor material and the electron donor material dissolved or dispersed in a solvent or a mixture of two or more solvents.
• the formulation may be deposited by any coating or printing method including, without limitation, spin-coating, dip-coating, roll-coating, spray coating, doctor blade coating, wire bar coating, slit coating, ink jet printing, screen printing, gravure printing and flexographic printing.
• the one or more solvents of the formulation may optionally comprise or consist of benzene substituted with one or more substituents selected from chlorine, C HO alkyl and Ci_io alkoxy wherein two or more substituents may be linked to form a ring which may be unsubstituted or substituted with one or more Ci_ 6 alkyl groups, optionally toluene, xylenes, trimethylbenzenes, tetramethylbenzenes, anisole, indane and its alkyl- substituted derivatives, and tetralin and its alkyl-substituted derivatives.
• substituents selected from chlorine, C HO alkyl and Ci_io alkoxy wherein two or more substituents may be linked to form a ring which may be unsubstituted or substituted with one or more Ci_ 6 alkyl groups, optionally toluene, xylenes, trimethylbenzenes, tetramethylbenzenes, anisole,
• the formulation may comprise a mixture of two or more solvents, preferably a mixture comprising at least one benzene substituted with one or more substituents as described above and one or more further solvents.
• the one or more further solvents may be selected from esters, optionally alkyl or aryl esters of alkyl or aryl carboxylic acids, optionally a C HO alkyl benzoate, benzyl benzoate or dimethoxybenzene.
• a mixture of trimethylbenzene and benzyl benzoate is used as the solvent.
• a mixture of trimethylbenzene and dimethoxybenzene is used as the solvent.
• the formulation may comprise further components in addition to the electron acceptor, the electron donor and the one or more solvents.
• adhesive agents, defoaming agents, deaerators, viscosity enhancers, diluents, auxiliaries, flow improvers colourants, dyes or pigments, sensitizers, stabilizers, nanoparticles, surface-active compounds, lubricating agents, wetting agents, dispersing agents and inhibitors may be mentioned.
• the organic photodetector as described herein may be used in a wide range of applications including, without limitation, detecting the presence and / or brightness of ambient light and in a sensor comprising the organic photodetector and a light source.
• the photodetector may be configured such that light emitted from the light source is incident on the photodetector and changes in wavelength and / or brightness of the light may be detected.
• the sensor may be, without limitation, a gas sensor, a biosensor, an X-ray imaging device, a motion sensor (for example for use in security applications) a proximity sensor or a fingerprint sensor.
• the photodetector may be form part of a 1D or 2D array in an image sensor.
• the photodetector may be part of an array of photodetectors in a camera image sensor. Examples
• Devices were formed using Donor Polymer 1 and either fullerene C60PCBM or IEICO- 4F as the acceptor.
• Donor Polymer 1 has the structure:
• the FUMO energy levels reported herein were determined using square wave voltammetry (SWV) at room temperature in solution.
• SWV square wave voltammetry
• the apparatus to measure HOMO or FUMO energy levels by SWV may comprise a cell containing tertiary butyl ammonium perchlorate or tertiary butyl ammonium hexafluorophosphate in acetonitrile; a glassy carbon working electrode; a platinum counter electrode and a leak free Ag/AgCI reference electrode.
• Ferrocene is added directly to the existing cell at the end of the experiment for calculation purposes where the potentials are determined for the oxidation and reduction of ferrocene versus Ag/AgCI using cyclic voltammetry (CV).
• LUMOs of the acceptor compounds were measured by square wave voltammetry using a CHI 660D Potentiostat with a 3mm diameter glassy carbon working electrode Leak free Ag/AgCI reference electrode Pt wire auxiliary or counter electrode and 0.1 M tetrabutylammonium hexafluorophosphate in acetonitrile.
• the sample was dissolved in toluene (3mg/ml) and spun at 3000rpm directly on to the glassy carbon working electrode.
• LUMO 4.8-E ferrocene (peak to peak average) - E reduction of sample (peak maximum).
• HOMO 4.8-E ferrocene (peak to peak average) + E oxidation of sample (peak maximum).
• the square wave voltammetry experiment may be run at l5Hz frequency; 25mV amplitude and 0.004V increment steps. Results are calculated from 3 freshly spun film samples for both the HOMO and LUMO data.
• C 60 PCBM has a LUMO level of 3.81 eV
• IEICO-4F has a LUMO level of 3.91 eV. Comparative Device 1
• a device having the following structure was prepared:
• a glass substrate coated with a patterned layer of indium-tin oxide (ITO) was treated with polyethyleneimine (PEIE) to modify the work function of the ITO.
• PEIE polyethyleneimine
• a ca. 800 nm thick bulk heterojunction layer of a mixture of Donor Polymer 1 and acceptor compound Q,oPCBM was deposited over the modified GGO layer by bar coating from a l,2,4-trimethylbenzene : l,2-dimethoxybenzene solvent mixture in a donor : acceptor mass ratio of 1:2.
• An anode (Clevios HIL-E100) available from Heraeus was formed over the donor / acceptor mixture layer by spin-coating.
• a device was formed as described for Comparative Device 1 except that a bulk heterojunction layer of a mixture of Donor Polymer 1 and IEICO-4F as the acceptor compound was deposited over the modified GGO layer by spin-coating from 1,2,4- trimethylbenzene: benzyl benzoate in a donor : acceptor weight ratio of 1:1.5.

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