WO2019193331A2 - Photodétecteur organique à infrarouge proche - Google Patents

Photodétecteur organique à infrarouge proche Download PDF

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WO2019193331A2
WO2019193331A2 PCT/GB2019/050954 GB2019050954W WO2019193331A2 WO 2019193331 A2 WO2019193331 A2 WO 2019193331A2 GB 2019050954 W GB2019050954 W GB 2019050954W WO 2019193331 A2 WO2019193331 A2 WO 2019193331A2
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organic photodetector
group
organic
independently selected
substituted
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PCT/GB2019/050954
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WO2019193331A3 (fr
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Jeremy Burroughes
Gianluca BOVO
Nir YAACOBI-GROSS
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Cambridge Display Technology Limited
Sumitomo Chemical Company Limited
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Priority to CN201980030407.XA priority Critical patent/CN112243538A/zh
Priority to JP2020553622A priority patent/JP7473477B2/ja
Publication of WO2019193331A2 publication Critical patent/WO2019193331A2/fr
Publication of WO2019193331A3 publication Critical patent/WO2019193331A3/fr

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    • 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
    • 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
    • H10K85/621—Aromatic anhydride or imide compounds, e.g. perylene tetra-carboxylic dianhydride or perylene tetracarboxylic di-imide
    • 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
    • H10K30/20—Organic devices sensitive to infrared radiation, light, electromagnetic radiation of shorter wavelength or corpuscular radiation comprising organic-organic junctions, e.g. donor-acceptor junctions
    • H—ELECTRICITY
    • H10—SEMICONDUCTOR DEVICES; ELECTRIC SOLID-STATE DEVICES NOT OTHERWISE PROVIDED FOR
    • H10K—ORGANIC ELECTRIC SOLID-STATE DEVICES
    • H10K85/00—Organic materials used in the body or electrodes of devices covered by this subclass
    • H10K85/10—Organic polymers or oligomers
    • H10K85/111—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
    • H10K85/60—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
    • 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
    • H10K85/6576—Polycyclic condensed heteroaromatic hydrocarbons comprising only sulfur in the heteroaromatic polycondensed ring system, e.g. benzothiophene
    • 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
    • H10K30/50—Photovoltaic [PV] devices
    • Y—GENERAL TAGGING OF NEW TECHNOLOGICAL DEVELOPMENTS; GENERAL TAGGING OF CROSS-SECTIONAL TECHNOLOGIES SPANNING OVER SEVERAL SECTIONS OF THE IPC; TECHNICAL SUBJECTS COVERED BY FORMER USPC CROSS-REFERENCE ART COLLECTIONS [XRACs] AND DIGESTS
    • Y02—TECHNOLOGIES OR APPLICATIONS FOR MITIGATION OR ADAPTATION AGAINST CLIMATE CHANGE
    • Y02E—REDUCTION OF GREENHOUSE GAS [GHG] EMISSIONS, RELATED TO ENERGY GENERATION, TRANSMISSION OR DISTRIBUTION
    • Y02E10/00—Energy generation through renewable energy sources
    • Y02E10/50—Photovoltaic [PV] energy
    • Y02E10/549—Organic PV cells

Definitions

  • the disclosure relates to photoactive compounds and their use in organic electronic devices, in particular organic photodetectors, and more particularly but not by way of limitation organic photodetectors for detecting wavelengths greater than goo nm or 1000 nm.
  • organic electronic devices comprising organic semiconductor materials are known, including organic light-emitting devices, organic field effect transistors, organic photovoltaic devices and organic photodetectors (OPDs).
  • organic light-emitting devices including organic light-emitting devices, organic field effect transistors, organic photovoltaic devices and organic photodetectors (OPDs).
  • OPDs organic photodetectors
  • CN106025073 discloses an organic solar cell employing a ternary component as an active layer.
  • CN106058056 discloses an active layer of an organic solar cell and a preparation method of the active layer.
  • CN108084409 discloses a wide bandgap organic semiconductor material.
  • U.S. 2018/0047862 relates to photoconversion devices, such as photovoltaic cells or photodetectors.
  • WO 2018/065352 relates to an organic photodetector (OPD) comprising a photoactive layer that contains an electron acceptor and an electron donor; the acceptor being an n-type semiconductor, which is a small molecule that does not contain a fullerene moiety, and the electron donor, being a p-type semiconductor, which is a conjugated copolymer, comprising donor and acceptor units.
  • OPD organic photodetector
  • WO 2018/078080 relates to organic semiconductor compounds containing a polycyclic unit as organic semiconductors.
  • U.S. 6,972,431 discloses organic photodetectors having a reduced dark current.
  • WO 2017/117477 discloses a-substituted PDI derivatives as small molecular and polymerized electron acceptors in organic photovoltaic cells.
  • U.S. 2017/ 0057962 discloses non-fullerene electron acceptors for highly efficient OPVs.
  • WO 2017/191468 discloses non-fullerene electron acceptors which maybe used in organic optical or electronic devices.
  • CN106025073 discloses organic solar cells.
  • WO 2013/ 182847 discloses novel organic compounds for use as electron acceptors.
  • U.S. 7,893,428 discloses photosensitive organic semiconductor compositions. Baran et al, Energy Environ. Sci., 2016, 3783-3793 discloses using non-fullerene acceptors in organic solar cells.
  • Hu et al, Polym. Chem., 2017, 528-536 discloses dark current reduction strategies using edge-on aligned donor polymers for high detectivity and responsivity organic photodetectors.
  • U.S. 8,853,679 relates generally to organic semiconductors and in particular to organic semiconductors for forming part of a thin film transistor.
  • Zhao et al, J. Am. Chem. Soc., 2017, 7148-7151 discloses that a new polymer donor (PBDB-T-SF) and a new small molecule acceptor (IT-4F) for fullerene-free organic solar cells (OSCs) were designed and synthesised.
  • PBDB-T-SF polymer donor
  • IT-4F small molecule acceptor
  • Lin et ah, Adv. Mater., 2015, 1170-1174 discloses the design and synthesis of a novel electron acceptor (ITIC) based on a bulky seven-ring fused core
  • WO 2017/125719 discloses organic photodiodes for use as photodetectors. It shows the use of fullerene derivatives in order to reduce dark currents in organic photodiodes.
  • Miao et ah Adv. Opt. Mater., 2016, 1711-1717 relates to organic photodetectors with tunable spectral response under bi-directional bias.
  • an organic photodetector comprising: first and second electrodes and a photosensitive organic layer positioned between the electrodes.
  • the photosensitive organic layer comprises a donor compound and an acceptor compound, wherein the acceptor compound does not comprise a fullerene group and wherein the LUMO energy level of the acceptor compound is equal to or deeper than the LUMO energy level of fullerene derivative C70IPH.
  • the photosensitive organic layer comprises a non- fullerene photosensitive organic layer. Applicants have found that such non- fullerene photosensitive organic layers can provide organic photo-sensors with low dark current, high EQE and/or that operate at wavelengths in excess of 900 nm, 1000 nm and/ or 1100 nm.
  • the OPD is connected to a voltage source such that a reverse bias maybe applied to it in operation.
  • the acceptor compound is represented by General
  • each of R 11 , R 12 , R 1 s, Ru, R 1 5 are each independently selected from one of: H, an electron withdrawing group such as halogen, CN, N0 2 , CF 3 , carbonyl, or heteroaryl which is unsubstituted or substituted with one or more substituents, or either of the following formulae (VIII) and (IX):
  • R 16 and R 1 ? are each independently selected from the group consisting of: H; branched, linear or cyclic C 1-20 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 maybe replaced with F; and aryl or heteroaryl which is substituted or unsubstituted with one or more substituents.
  • R 1 , R 20 R 21 , R 22 and R 2 3 are H or an electron withdrawing group such as halogen, selected from the group consisting of: Cl, Br, I or F; or CN, NO2, CF3, carbonyl or heteroaryl which is unsubstituted or substituted with one or more substituents, and each of R 16 and R 1 ? is -(CH 2 )nCH 3, where n is an integer selected from 1 to 20.
  • At least one occurrence of at least one of R 20 -R 2 3 is F.
  • R 20 -R 2 3 are each H or F.
  • R 11 , R 12 , R*3 and R 1 4 are formula (VIII), where n is 5.
  • R 11 , R 12 , R*3 and Ru are formula (IX), where n is 5.
  • the compound of formula (V) has formula (Va):
  • each fluorine may independently be in the 3-, 4-, 5- or 6- positions on the benzene rings. In some embodiments, each fluorine is in the 3-, 4-, 5- or 6- position on the benzene ring. Alternatively, one fluorine is in the 3-,
  • the acceptor compound is ITIC, ITIC-2F or ITIC-Th. In some embodiments, the acceptor compound is represented by General Formula (I):
  • each R 1 is independently selected from the group consisting of: H; branched, linear or cyclic C 1-20 alkyl wherein one or more non-adjacent, non-terminal C atoms maybe replaced with O, S, CO or COO and one or more H atoms maybe replaced with F; and aryl or heteroaryl which is substituted or unsubstituted with one or more substituents;
  • each of R 2 and R3 are independently selected from the group consisting of: H; branched, linear or cyclic C1-20 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 maybe replaced with F; aryl or heteroaryl which is substituted or unsubstituted with one or more substituents; and a group having the following formula (II):
  • each of R4 and R> are independently selected from the group consisting of: H; branched, linear or cyclic C 1-20 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 maybe replaced with F; and aryl or heteroaryl which is substituted or unsubstituted with one or more substituents.
  • R 1 and R4 are each independently selected from a group having the following formula (IV):
  • each of R9 and R 10 are independently selected from the group consisting of: -CH 3 and -(CH 2 )nCH 3 , wherein n is an integer selected from 1-20.
  • the acceptor compound has the following formula (XII):
  • R l8 has the following formula (IV):
  • each of R9 and R 10 are independently selected from the group consisting of: -CH 3 and -(CH 2 )nCH 3 , wherein n is an integer selected from 1-20. In some embodiments, n is 4 or 5.
  • the donor compound is a semiconducting polymer.
  • the first electrode is an anode and the second electrode is a cathode.
  • the weight ratio of the donor compound to the acceptor compound is from about 1: 0.5 to about 1:1.2.
  • a sensor comprising a light source and an organic photodetector as described herein, wherein the organic photodetector is configured to receive light from the light source.
  • a method of detecting light comprising measurement of a
  • the method of detecting light comprises measurement of the photocurrent generated by light incident on the organic photodetector and emitted from the light source of the sensor according to the second aspect.
  • a fourth aspect of some embodiments of the present invention there is provided a use of a compound that does not comprise a fullerene group having a LUMO energy level and is deeper than the LUMO energy level of fullerene derivative C70IPH in a photosensitive layer of an organic photodetector to reduce dark current.
  • Figure 1 illustrates an organic photodetector according to an embodiment of the invention
  • Figures 2, 3 and 6 are graphs of current density vs applied voltage for devices in dark conditions according to embodiments and a comparative device
  • Figures 4, 5 and 7 are graphs of EQE vs wavelength of devices according to embodiments and a comparative device.
  • 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. It is therefore an object of some of the embodiments of the present invention to provide an OPD having low dark current. It is a further object of some of the embodiments of the present invention to provide an OPD having low dark current and good external quantum efficiency (EQE).
  • EQE external quantum efficiency
  • Organic electronic devices comprising organic semiconductor materials include organic light-emitting devices, organic field effect transistors, organic
  • OPD photovoltaic devices and OPDs.
  • OPDs It maybe necessary to balance the functionality of the organic semiconductor material to provide a low dark current (the current produced by the OPD when no light is present as a result of the reverse bias applied to the OPD) with the EQE of the organic semiconductor material.
  • a low dark current the current produced by the OPD when no light is present as a result of the reverse bias applied to the OPD
  • EQE the organic semiconductor material with a good EQE also produce a high dark current.
  • an OPD may be desirable to operate at wavelengths outside of and/ or where there are gaps in the wavelengths of sunlight, visible light in the sensing environment. For example, sunlight at wavelengths around 940 nm may be absorbed in the atmosphere creating a gap at this wavelength and light emitting devices may operate in the visible spectrum and not produce any output at wavelengths beyond 900 nm. Operating an OPD sensor at such wavelengths reduces the interference from the sunlight/ visible light.
  • an organic semiconductor material with an EQE that maybe considered low maybe useful for an OPD that operates in such wavelengths, absent interferences (as such for purposes of this disclosure the term“high EQE” means a high EQE with respect to an OPD working in the near infrared spectrum).
  • OPVs it may not be desirable to operate at such wavelengths, >900 nm, as the OPV uses the electromagnetic radiation present in the environment.
  • FIG. 1 illustrates an OPD according to an embodiment of the invention.
  • the OPD comprises a cathode 103 supported by a substrate 101, an anode 107 and a bulk heterojunction layer 105 located 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 photodetectors as described in this disclosure maybe 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 maybe part of an array in an image sensor of a camera.
  • the voltage applied to the photodetectors maybe varied.
  • the photodetectors may be continuously biased when in use.
  • the OPD may be incorporated into a sensor comprising a light source and the OPD may be 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.
  • a high dark current in photodetectors limits the detectible optical input signal due to a low signal-to-noise ratio.
  • acceptor compounds as described herein provide OPDs with dark currents of the order of at least 5 times or at least 10 times less than fullerene compounds such as C70IPH.
  • the acceptor compounds as described herein, according to some embodiments of the present disclosure provide EQEs of greater than 30% across a wide spectrum of wavelengths.
  • EQE’s of the order of 30% have even been obtained at wavelengths between 900 and 1000 nanometres and EQEs of the order between 5 and 20% have been shown at wavelengths up to 1100 nm.
  • the inventors have also surprisingly found that the acceptor compounds described herein provide for detection of longer wavelength applications in particular wavelengths of greater than 900 nm and greater than 1000 nm. As described above, the inventors have further found that the acceptor
  • the electron acceptor compounds described herein do not comprise a fullerene group, and are described hereinafter as“non-fullerene acceptors”.
  • the organic photodetector comprises:
  • a first electrode which may be the anode or the cathode
  • a second electrode which may be the other of the anode or the cathode
  • the photosensitive organic layer positioned between the electrodes, wherein the photosensitive organic layer comprises a donor compound and an acceptor compound, wherein the acceptor compound does not comprise a fullerene group and wherein the LUMO energy level of the acceptor compound is equal to or deeper than the LUMO energy level of fullerene derivative C70IPH.
  • references to a“deeper” LUMO energy level as used herein means further from vacuum level and reference to a“shallower” LUMO energy level as used herein means closer to vacuum level. It will therefore be understood that the LUMO energy level of an acceptor compound which does not comprise a fullerene group as described herein is further from vacuum level than the LUMO energy level of the fullerene derivative C70IPH.
  • the LUMO energy of the acceptor compound is at least 3.65, 3.66, 3.67, 3.68, 3.69, 3.70, 3.71, 3.72, 3.73, 3.74 or 3.75 eV deeper than the vacuum level as measured by square wave voltammetry.
  • non-fullerene acceptor compounds described herein may be small molecule non-fullerene acceptors (SM-NFAs).
  • SM-NFAs small molecule non-fullerene acceptors
  • the non-fullerene acceptor compound maybe a compound of General Formula m (I):
  • each R 1 is independently selected from the group consisting of: H; branched, linear or cyclic C 1-20 alkyl wherein one or more non-adjacent, non-terminal C atoms maybe replaced with O, S, CO or COO and one or more H atoms maybe replaced with F; and aryl or heteroaryl which is substituted or unsubstituted with one or more substituents;
  • each of R 2 and Rs are independently selected from the group consisting of: H; branched, linear or cyclic C 1-20 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 maybe replaced with F; aryl or heteroaryl which is substituted or
  • R4, R5, R 6 , R7 and R 8 are each independently selected from the group consisting of: H; branched, linear or cyclic C 1-20 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 maybe replaced with F; and aryl or heteroaryl which is substituted or unsubstituted with one or more substituents.
  • each R 1 , R4 and R 6 is independently selected from a branched, linear or cyclic C 1-20 alkyl group.
  • each R 1 , R4 and R 6 is independently selected from a group having the following formula (IV):
  • each of R9 and R 10 are independently selected from the group consisting of: H; branched, linear or cyclic C1-20 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 maybe replaced with F; and aryl or heteroaryl which is substituted or unsubstituted with one or more substituents.
  • each of R9 and R 10 are independently selected the group consisting of: -CH 3 and -(CH 2 ) n CH 3 , wherein n is an integer selected from 1-20.
  • each of R9 and R 10 are independently selected the group consisting of:
  • each of R9 and R 10 is - (CH 2 ) 4 CH 3 or -(CH 2 ) 5 CH 3 .
  • each R 2 is independently selected from the group consisting of: H; branched, linear or cyclic C - 20 alkyl.
  • each R 2 is H.
  • R 3 is selected from an aryl or heteroaryl which is substituted or unsubstituted with one or more substituents.
  • R 3 is selected from a group according to formula (II) or (III).
  • R 3 is formula (II).
  • each R4 is independently selected from a branched, linear or cyclic C - 20 alkyl group.
  • each R4 is independently selected from a group having the following formula (IV):
  • each of R9 and R 10 are independently selected from the group consisting of: H; branched, linear or cyclic C 1-20 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 i1o0 atoms maybe replaced with F; and aryl or heteroaryl which is substituted or unsubstituted with one or more substituents.
  • each of R9 and R 10 are independently selected the group consisting of: -CH 3 and -(CH 2 ) n CH 3 , wherein n is an integer selected from 1-20.
  • each of R9 and R 10 are independently selected the group consisting of: -CH 3, -(CH 2 ) 4 CH 3 and -(CH 2 ) 5 CH 3 .
  • each of R9 and R io is -(CH 2 ) 4 CH 3 or -(CH 2 ) 5 CH 3 .
  • each R> is independently selected from the group consisting of: H; branched, linear or cyclic C - 20 alkyl.
  • each R> is H.
  • each R 6 is independently selected from a branched, linear or cyclic C - 20 alkyl group.
  • each R 6 is independently selected from a group having the following formula (IV): wherein each of R9 and R 10 are independently selected from the group consisting of: H; branched, linear or cyclic C1-20 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 maybe replaced with F; and aryl or heteroaryl which is substituted or unsubstituted with one or more substituents.
  • R9 and R 10 are independently selected from the group consisting of: H; branched, linear or cyclic C1-20 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 maybe replaced with F; and aryl or heteroaryl which is substituted or unsubstituted with one or more substituents.
  • each of R9 and R 10 are independently selected the group consisting of: -CH 3 and -(CH 2 ) n CH 3 , wherein n is an integer selected from 1-20.
  • each of R9 and R 10 are independently selected the group consisting of: -CH 3 , -(CH 2 ) 4 CH 3 and -(CH 2 ) 5 CH 3 .
  • each of R9 and R 10 is - (CH 2 ) 4 CH 3 or -(CH 2 ) 5 CH 3 .
  • each of R7 and R 8 are independently selected from the group consisting of: H; branched, linear or cyclic C - 20 alkyl.
  • each of R? and R 8 are H.
  • the non-fullerene acceptor compound may be a compound of General Formula (V): wherein each of R 11 , R 12 , R * 3, R 1 4, Rry R 2 o ; R ; R anc[ R 3 are independently selected from the group consisting of: H; an electron withdrawing group such as a halogen (including Cl, Br, I or F); or CN, NO2, CF3, carbonyl or heteroaryl which is unsubstituted or substituted with one or more substituents; branched, linear or cyclic C - 20 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 maybe replaced with F; and aryl or heteroaryl which is unsubstituted or substituted with one or more substituents.
  • V General Formula
  • each of R 11 , R 12 , R*3, R 1 b Rry R 20 , R 21 , R 22 and R 2 3 are independently selected from one of either the following formulae (VI) and (VII):
  • each of R 11 , R 12 , R*3, R 1 b Rry R 20 , R 21 , R 22 and R 2 3 are independently selected from one of either formulae (VI) and (VII) wherein one or more H atoms of each of formula (VI) and (VII) are independently replaced with a substituent selected from the group consisting of: branched, linear or cyclic C 1-20 alkyl wherein one or more non-adjacent, non-terminal C atoms maybe replaced with O, S, CO or COO and one or more H atoms maybe replaced with F; and aryl or heteroaryl which is unsubstituted or substituted with one or more substituents.
  • each of R 11 , R 12 , R 1 ! , Ru are independently selected from the group consisting of: H; an electron withdrawing group such as a halogen (including Cl, Br, I or F); or CN, N02, CF3, carbonyl or heteroaryl which is unsubstituted or substituted with one or more substituents; ; formulae (VI) and (VII); wherein one or more H atoms of each of formula (VI) and (VII) are independently replaced with a substituent selected from the group consisting of: branched, linear or cyclic C 1-20 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 maybe replaced with F; and aryl or heteroaryl which is unsubstituted or substituted with one or more substituents; and R 1 , R 20 , R 21 , R 22 and R 2 3 are selected from the group consisting of: H; an electron withdraw
  • each of R 11 , R 12 , R*3, R 1 4 are independently selected from either formulae (VI) and (VII), wherein one or more H atoms of each of formula (VI) and (VII) are independently replaced with a substituent selected from the group consisting of: branched, linear or cyclic C 1-20 alkyl wherein one or more non-adjacent, non-terminal C atoms maybe replaced with O, S, CO or COO and one or more H atoms maybe replaced with F; and aryl or heteroaryl which is unsubstituted or substituted with one or more substituents, R 1 is H and each of R 20 , R 21 , R 22 and R 2 3 is H.
  • R 11 , R 12 , R*3, Ru are selected from either formulae (VI) or (VII), wherein one or more H atoms of each of formula (VI) and (VII) are independently replaced with a substituent selected from the group consisting of: branched, linear or cyclic C 1-20 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 maybe replaced with F; and aryl or heteroaryl which is unsubstituted or substituted with one or more substituents, R 1 is H and each of R 20 , R 21 , R 22 and R 2 3 is an electron withdrawing group, preferably a halogen selected from F, Cl, I,
  • the electron withdrawing group may comprise CN, NO2, CF3, carbonyl or heteroaryl which is substituted or unsubstituted with one or more substituents.
  • R 11 , R 12 , R 13 , R 1 4 are selected from either of the following formulae (VIII) and (IX), R 15 is H and each of R 20 , R 21 , R 22 and R 23 is H or an electron withdrawing group, preferably a halogen selected from F, Cl, I, Br:
  • R 16 and R 1 ? are each independently selected the group consisting of: - CH 3 and -(CH 2 )nCH 3 , wherein n is an integer selected from 1-20.
  • R 11 , R 12 , R 13 , R ⁇ are selected from either of the following formulae (X) and (XI), R 13 is H and each of R 20 , R 21 , R 22 and R 23 is independently selected from H or a halogen selected from F, Cl, I, Br; or CN, NO2, CF3, carbonyl or heteroaryl which is unsubstituted or substituted with one or more substituents:
  • R 11 , R 12 , R*3, R 1 4 are selected from either of the following formulae (X) and (XI), R 1 ⁇ is H and each of R 20 , R 21 , R 22 and R 2 3 is H:
  • R 11 , R 12 , R 1 3, RH are selected from either of the following formulae (X) and (XI), R 1 > is H and each of R 20 , R 21 , R 22 and R 2 3 is independently selected from a halogen selected from: F, Cl, I, Br:
  • R 11 , R 12 , R*3, R 1 4 are selected from either of the following formulae (X) and (XI), R 1 is H, three of R 20 , R 21 , R 22 and R 2 3 is H and one of R 20 , R 21 , R 22 and R 2 3 is independently selected from a halogen selected from: F, Cl, I, Br:
  • R 11 , R 12 , R*3, R 1 4 are selected from either of the following formulae (X) and (XI), R 1 is H, two of R 20 , R 21 , R 22 and R 2 3 is H and two of R 20 , R 21 , R 22 and R 2 3 are independently selected from a halogen selected from: F, Cl, I, Br:
  • R 11 , R 12 , R 1 ! , RH are selected from either of the following formulae (X) and (XI), R 1 is H, R 20 and R 2 3 are H and R 21 and R 22 are independently selected from a halogen selected from: F, Cl, I, Br:
  • R 15 is H and each of R 20 , R 21 , R 22 and R 2 3 is independently selected from H or a halogen selected from: F, Cl, I, Br.
  • the non-fullerene acceptor compound has an external quantum efficiency of at least io%, optionally at least 15% or at least 20%, as measured in a device as described in Device Example 1.
  • ITIC-2F has a LUMO level that is deeper than the non-fluorinated acceptor, ITIC.
  • the donor compound (p-type) is not particularly limited and maybe
  • 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.
  • exemplary p- type donor polymers polymers selected from conjugated hydrocarbon or heterocyclic polymers including polyacene, polyaniline, polyazulene,
  • Preferred examples of p- type donors are copolymers of polyfluorenes and polythiophenes, each of which maybe 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 electron donor preferably comprises a repeat unit of formula (XIII):
  • R 2 4 in each occurrence is independently H or a substituent.
  • each R 2 4 is independently selected from the group consisting of:
  • non-terminal as used herein is meant a carbon atom other than the methyl group of a linear alkyl (n-alkyl) chain and the methyl groups of a branched alkyl chain.
  • a polymer comprising a repeat unit of formula (XIII) is preferably a copolymer comprising one or more co-repeat units.
  • the one or more co-repeat units may comprise or consist of one or more of C6- 20 monocyclic or polycyclic arylene repeat units which maybe unsubstituted or substituted with one or more substituents; 5-20 membered monocyclic or polycyclic heteroarylene repeat units which maybe unsubstituted or substituted with one or more substituents.
  • the one or more co-repeat units may have formula (XIV):
  • Ar 1 in each occurrence is an arylene group or a heteroarylene group; m is at least 1; R 2 is a substituent; R 2 in each occurrence is independently a
  • each R 2 is independently selected from the group consisting of a linear, branched or cyclic C1-20 alkyl wherein one or more non-adjacent, non terminal C atoms of the C1-20 alkyl may be replaced with O, S, COO or CO.
  • Two groups R 2 s maybe linked to form a Ci-10 alkylene group wherein one or more non-adjacent C atoms of the alkylene group may be replaced with O, S, COO or CO.
  • n 2
  • each Ar 1 is independently a 5 or 6 membered heteroarylene group, optionally a heteroarylene group selected from the group consisting of thiophene, furan, selenophene, pyrrole, diazole, triazole, pyridine, diazine and triazine, preferably thiophene.
  • repeat unit of formula (XIV) has formula (XlVa):
  • the groups R 2 are linked to form a 2-5 membered bridging group.
  • the bridging group has formula -0-C(R 26 ) 2 - wherein R 26 in each occurrence is independently H or a substituent. Substituents R 26 are optionally selected from C1-20 alkyl. Preferably each R 26 is H.
  • Exemplary donor polymers are disclosed in WO2013/ 051676 and
  • the weight ratio of the donor compound to the acceptor compound is about 1:0.5, 1:0.6, 1:0.7, 1:0.8, 1:0.9, 1:1, 1:1.1, 1:1.2, 1:1.3, 1:14, 1:1.5, 1:1.6, 1:1.7, 1:1.8, 1:1.9 or 1:2. In some embodiments, 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).
  • 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 metal may be aluminium or silver or gold.
  • a bi-layer electrode maybe used.
  • the electrode may be an indium tin oxide (ITO)/silver bi-layer, an ITO/aluminium bi-layer or an ITO/gold bi-layer.
  • ITO indium tin oxide
  • 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 maybe less than about 3 cm 2 , less than about 2 cm 2 , less than about 1 cm 2 , less than about 0.75 cm 2 , less than about 0.5 cm 2 or less than about 0.25 cm 2 .
  • the substrate maybe, without limitation, a glass or plastic substrate.
  • the substrate can be described as an inorganic semiconductor.
  • the substrate maybe 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 maybe 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, inkjet 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, Ci-10 alkyl and Ci-10 alkoxy wherein two or more substituents may be linked to form a ring which may be unsubstituted or substituted with one or more C1-6 alkyl groups, optionally toluene, xylenes, trimethylbenzenes, tetramethylbenzenes, anisole, indane and its alkyl-substituted derivatives, and tetralin and its alkyl- substituted derivatives.
  • the formulation may comprise a mixture of two or more solvents, preferably a mixture comprising at least one benzene substituted with one or more
  • the one or more further solvents may be selected from esters, optionally alkyl or aryl esters of alkyl or aryl carboxylic acids, optionally a Ci-io alkyl benzoate, benzyl benzoate or dimethoxybenzene.
  • esters optionally alkyl or aryl esters of alkyl or aryl carboxylic acids
  • benzyl benzoate optionally a Ci-io alkyl benzoate
  • benzyl benzoate or dimethoxybenzene optionally a Ci-io 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 maybe 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 organic photodetector may be configured such that light emitted from the light source is incident on the organic photodetector and changes in wavelength and/ or brightness of the light may be detected.
  • the sensor maybe, 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 organic photodetector maybe form part of a lD or 2D array in an image sensor.
  • the organic photodetector may be part of an array of organic photodetector in a camera image sensor.
  • a device having the following structure was prepared:
  • Cathode/Donor Acceptor layer/Anode A glass substrate coated with a patterned layer of ITO was treated with
  • PEIE polyethyleneimine
  • a bulk heterojunction layer of a mixture of a Donor Polymer l and acceptor compound C70IPH was deposited over the modified ITO layer by bar coating from 1,2,4-trimethylbenzene : benzyl benzoate in a donor : acceptor mass ratio of
  • An anode (Clevios HIL-E100) available from Heraeus was formed over the donor / acceptor mixture layer by spin-coating.
  • Donor Polymer 1 has the structure:
  • Devices were formed as described for Comparative Device 1 except that a bulk heterojunction layer of a mixture of Donor Polymer 1 and either di-PDI, ITIC or ITIC-Th as the acceptor compound was deposited over the modified ITO layer by spin-coating from 1,2,4-trimethylbenzene : benzyl benzoate in a donor : acceptor mass ratio of 1:1.
  • Example 1 When the dark current and EQE measurements for Example 1 are considered together, it will be appreciated that, overall, the devices of Example 1 exhibit an improved signal-to-noise ratio compared with Comparative Device 1.
  • a device having the following structure was prepared:
  • a glass substrate coated with a patterned layer of ITO was treated with PEIE to modify the work function of the ITO.
  • a bulk heterojunction layer of a mixture of a donor polymer and acceptor compound C60PCBM was deposited over the modified ITO layer by bar coating from 1,3-dimethoxybenzene : benzyl benzoate in a donor : acceptor mass ratio of 1:1.75.
  • 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 2 except that ITIC-2F was used as the acceptor compound in place of C60PCBM in a donor : acceptor mass ratio of 1:1.5.
  • the EQE of the device made according to Example 2 was measured in reverse bias (3 V). With reference to Figure 7, a slight reduction in the EQE was observed for the device comprising ITIC-2F. However, when the dark current and EQE measurements for Example 2 are considered together, it will be appreciated that, overall, the device of Example 2 exhibits an improved signal-to-noise ratio compared with Comparative Device 2.
  • the apparatus to measure HOMO or LUMO 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).
  • the sample is dissolved in Toluene (3 mg/ml) and spun at 3000 rpm 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).

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Abstract

La présente invention concerne un photodétecteur organique comprenant une couche organique photosensible positionnée entre deux électrodes. La couche organique photosensible est constituée d'un composé donneur et d'un composé accepteur, et le composé accepteur est un composé non fullerène qui ne comprend pas de groupe fullerène. Le niveau d'énergie LUMO du composé accepteur est le même ou plus profond que le niveau d'énergie LUMO d'un dérivé de fullerène, tel que C70IPH. La couche organique photosensible produit un faible courant d'obscurité et une bonne EQE et peut fonctionner dans l'infrarouge proche.
PCT/GB2019/050954 2018-04-03 2019-04-03 Photodétecteur organique à infrarouge proche WO2019193331A2 (fr)

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