WO2013182847A1 - Composés organiques accepteurs d'électrons - Google Patents

Composés organiques accepteurs d'électrons Download PDF

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WO2013182847A1
WO2013182847A1 PCT/GB2013/051484 GB2013051484W WO2013182847A1 WO 2013182847 A1 WO2013182847 A1 WO 2013182847A1 GB 2013051484 W GB2013051484 W GB 2013051484W WO 2013182847 A1 WO2013182847 A1 WO 2013182847A1
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compound
electron
electron acceptor
energy
unoccupied molecular
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PCT/GB2013/051484
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English (en)
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Tao Liu
Alessandro TROISI
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The University Of Warwick
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    • C—CHEMISTRY; METALLURGY
    • C07—ORGANIC CHEMISTRY
    • C07D—HETEROCYCLIC COMPOUNDS
    • C07D519/00—Heterocyclic compounds containing more than one system of two or more relevant hetero rings condensed among themselves or condensed with a common carbocyclic ring system not provided for in groups C07D453/00 or C07D455/00
    • 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
    • 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
    • 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
    • H10K85/623—Polycyclic condensed aromatic hydrocarbons, e.g. anthracene containing five rings, e.g. pentacene
    • 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
    • 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
    • H10K85/656—Aromatic compounds comprising a hetero atom comprising two or more different heteroatoms per ring
    • H10K85/6565—Oxadiazole compounds
    • 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 present invention relates to novel organic compounds for use as electron acceptors, the same in combination with an electron donor compound, materials containing the same, and electronic devices comprising the same such as photovoltaic cells, light emitting diodes, transistors and photocatalytic devices as well as processes for preparing such compounds and processes for preparing such devices.
  • the compounds described herein may be useful as substitutes for fullerene and its derivatives; that is they mimic the properties of fullerene and its derivatives as an electron acceptor in combination with an electron donor compound, and demonstrate improvements compared to fullerene and its derivatives when used in this way, but the invention may also be seen in a more general context as providing a novel approach for providing electron acceptor compounds exhibiting pre-specified characteristics.
  • the ability to support electron transport in three dimensions may contribute to the high effectiveness of fullerene-based acceptors.
  • a large number of organic synthesis groups are designing alternative electron acceptor materials (both polymeric and molecular) trying to increase the pool of electron acceptors; for example see Sonar, P. et al, Energy & Environmental Science 2011, 4, (5), 1558-1574.8 and Anthony, J. E., Chemistry of Materials 2010, 23, (3), 583-590. Extending the pool of available electron acceptor compounds beyond fullerene derivatives will increase immediately the possible blends that can be considered and pave the way to address some of the limitations of the fullerene derivative, e.g. the very limited light adsorption and the very high cost of the most efficient derivatives.
  • the invention provides compounds which are useful as electron acceptor compounds.
  • the present invention provides compounds of the following formula:
  • each sp2 carbon atom is substituted by one R group, wherein the R groups are identical and lay perpendicular to the pi plane of the sp2 carbon atoms;
  • each R is identical and is a chromophore
  • each X is independently selected from H or a substituent that does not have unoccupied orbitals at lower energy than R.
  • the present invention provides a combination of an electron donor compound and an electron acceptor compound, wherein the electron acceptor compound is a compound described in the context of the first aspect.
  • the present invention provides a material comprising a combination of an electron donor compound and an electron acceptor compound as described above in the context of the second aspect.
  • the present invention provides the use of a compound of the present invention as an n-type semiconductor.
  • the present invention provides an electronic device comprising a combination of an electron donor compound and an electron acceptor compound as described above in the context of the second aspect, for example, a transistor, a light emitting diode, a photovoltaic cell or a photocatalytic device.
  • the invention provides the use of a compound of the present invention as an electron acceptor compound, for example for use in combination with an electron donor compound.
  • the invention provides a process for preparing a compound of the present invention.
  • the primary charge separation event in a donor-acceptor (DA) combination is the electron transfer between the photoexcited donor (D*) to the acceptor:
  • the anion of fullerene acceptors possesses such very low excited states, not visible spectroscopically because the relevant electronic transitions are forbidden, as has now been verified through quantum chemical calculations.
  • the first and second lowest excitation energies of [6o]PCBM are computed to be at 0.21 and 0.43 eV and they are dominated respectively by the transitions (using the orbital nomenclature of the neutral molecule). Similar low lying (and dark) excited states are found for the anion of the equally good electron acceptor
  • the electron acceptor compound exhibits an excited state of its anion at an energy level of less than 0.5 eV relative to the energy level of the neutral anion.
  • Figure 1 illustrates the electron transfer between electron orbitals of a donor (D) - acceptor (A) combination.
  • Figure i(a) provides a schematic of the one electron level at the interface between a donor (D) and a fullerene acceptor (A) with three unoccupied orbitals and therefore three possible electron transfer reactions with different rates.
  • D(LUMO) to A(LUM0+2) is fastest.
  • D(LUMO) to A(LUMO) is less fast.
  • Figure i(b) illustrates that in the presence of a single electron accepting lowest unoccupied molecular orbital (LUMO) at low energy the charge separation would be slower (less fast).
  • Figure i(c) illustrates that in the presence of a single electron accepting LUMO close to the donor's LUMO the reaction would be fast (fastest) but there would not be enough additional energy to promote the generation of fully separated electron and holes.
  • the second excited state has the largest charge separation rate k 3 because the separation takes place with no barrier (initial and final states are also very close in energy). As shown in Figure l, in the absence of the additional electron accepting orbital the charge separation would be slower ( Figure i(b)).
  • the present invention therefore provides a completely novel approach for providing fullerene mimics with the same electronic structure characteristics as fullerene. Furthermore, the same approach is equally useful in the search for alternative electron acceptor compounds for use in association with all types of electron donor compounds.
  • Such links may be carbon (C) with sp3 hybridization (chemically connected with four atoms), nitrogen (N) and phosphorous (P) with sp3 hybridization (chemically connected with three atoms, or four atoms as a positive ion, sulphur (S) and oxygen (O), e.g. non-conjugated alkyl links and the like.
  • the two chromophores R can be connected to two adjacent sp2 carbons (e.g. in ortho position of a phenyl ring) where they lay perpendicular to the pi plane of the linker.
  • the invention provides a compound of the following formula:
  • each sp2 carbon atom is substituted by one R group, wherein the R groups are identical and lay perpendicular to the pi plane of the sp2 carbon atoms;
  • each R is identical and is a chromophore
  • each X is independently selected from H or a substituent that does not have unoccupied orbitals at lower energy than R.
  • the two sp2 carbon atoms may, for example, be part of a phenyl ring, i.e. the chromophore R groups are substituted at the ortho position of the phenyl ring with respect to each other.
  • the compound of the invention has the formula RX 2 C-CX 2 R, preferably the formula RH 2 C-CH 2 R.
  • chromophore used herein should be understood to mean a group in a molecule that causes absorption of electromagnetic radiation, preferably in the ultraviolet or visible region.
  • the substituent R may be any chromophore but as illustrated in the above definition there must be at least two identical chromophore substituents in the compound. Small chemical modifications of the chromophore may of course be made, e.g. each individual chromophore may be adapted by the addition of substituents which can be used to fine tune the chromophore's energy levels. If necessary, these substituents can also be used to influence the solubility of the overall compound and improve other desired properties of the compound, e.g. the material morphology. However, the primary role of any such substituents is to fine tune the chromophore's energy levels. In this respect, each chromophore may be designed with respect to the acceptor to be used. In particular, each chromophore structure may be optionally substituted with any one or more of the following substituents: -NH2, -PH2, -CF3, -F, -C 6 H 5 O.
  • the chromophore R may be selected from the group consisting of:
  • R' is -H, -NH 2 , -Ph 2 or -CF3; wherein R' is -H, -CH 3 , or -NH 2
  • R' is -H or -F
  • R' is -H, or - C 6 ⁇ 5 O;
  • the electron acceptor compound is selected fro group consisting of:
  • the compound is selected from the group consisting of:
  • the compound is:
  • the compounds of the invention may be based on:
  • R can be a chromophore group connected to the central carbon through an aromatic carbon atom as in the example below:
  • R can be a group connected to the central carbon via an imide nitrogen (an easier to prepare molecule), such as:
  • these electron acceptors may belong to the D 2d or S 4 symmetry point group which sustain degenerate molecular orbitals and improve the likelihood of degeneracy in the LUMO.
  • the proposed acceptors extend in three dimensions, i.e., like fullerenes, they are expected to be strongly coupled with neighbouring molecule in all directions.
  • the symmetry of the molecule also guarantees that the molecular dipole moment is very low (or null if the molecule belongs to the point group D 2d or S 4 or D 2 ), i.e. the material, also in a glassy state, will have limited electrostatic disorder.
  • the substituent X may be the same or different and may be independently selected from any substituent that does not have unoccupied orbitals at lower energy than R, i.e. any substituent that does not interfere with the frontier orbitals of the chromophore.
  • group X maybe selected to increase solubility of the overall compound, to add new functionalities, or to control the material morphology.
  • X may be H or an organic fragment without a pi-conjugated fragment, such as an alkyl group (e.g. alkyl, preferably C 6-12 alkyl).
  • X is H.
  • the compounds disclosed above possess the characteristics required by an electron acceptor in organic photovoltaics.
  • the compounds possess a quasi degenerate set of LUMO orbitals based on the molecular orbital energy levels of the corresponding electron donor compound employed in organic photovoltaics.
  • the present invention allows the energy levels of the chromophore to be tuned with respect to the donor compound employed.
  • the compounds of the present invention preferably comprise at least two unoccupied molecular orbitals having energy levels between the energy level of the lowest unoccupied molecular orbital (LUMO) of the corresponding electron donor compound and about 1 eV less than the energy level of the lowest unoccupied molecular orbital (LUMO) of the corresponding electron donor compound; wherein one of said molecular orbitals is the lowest unoccupied molecular orbital (LUMO) of the compound of the present invention.
  • the compounds of the present invention may comprise at least two unoccupied molecular orbitals having energy levels between about -4.0 eV and -1.0 eV, preferably between about -3.6 eV and -2.2 eV; more preferably between about -3.5 eV and -2.6 eV.
  • the electron acceptor compounds of the present invention are coupled with an electron donor compound.
  • the compounds described above are therefore useful as electron acceptor compounds in combination with an electron donor compound.
  • the present invention provides a combination of an electron donor compound and an electron acceptor compound; wherein the electron acceptor compound is a compound according to any aspect/embodiment of the present invention.
  • the present invention provides a combination of an electron donor compound and an electron acceptor compound comprising an electron donor compound and an electron acceptor compound; wherein the electron acceptor compound is a compound according to any aspect/embodiment of the present invention comprising at least two unoccupied molecular orbitals having energy levels between the energy level of the lowest unoccupied molecular orbital (LUMO) of said electron donor compound and about 1 eV less than the energy level of the lowest unoccupied molecular orbital (LUMO) of said electron donor compound; wherein one of said molecular orbitals is the lowest unoccupied molecular orbital (LUMO) of the electron acceptor compound.
  • the combination of an electron donor compound and an electron acceptor compound may either be blended together or fully phase segregated.
  • the electron donor compound may be any compound that absorbs visible light.
  • the invention is exemplified with P3HT as the electron donor compound.
  • the present invention provides a material comprising a combination of an electron donor compound and an electron acceptor compound as described above optionally blended with one or more excipients.
  • the material may be a bulk material or a film, preferably a thin film.
  • the present invention provides the use of an electron acceptor compound of the present invention as an n-type semiconductor.
  • the present invention provides an electronic device comprising an electron acceptor compound according to any aspect/ embodiment of the invention; wherein the electronic device is a transistor.
  • the present invention provides an electronic device comprising a combination of an electron donor compound and an electron acceptor compound as described above.
  • the electronic device may be selected from a light emitting diode, a photovoltaic cell or a photocatalytic device.
  • the electronic device is a photovoltaic cell.
  • the present invention provides the use of a compound according to any aspect/ embodiment of the present invention as an electron acceptor compound, preferably for use in combination with an electron donor compound, more preferably in a photovoltaic cell.
  • the present invention provides a process for preparing a compound described above according to the present invention.
  • the compounds maybe prepared using conventional chemistry in which the chromophore substituents R are attached to the core structure of the electron acceptor compound.
  • the R groups may be attached to the core structure via one or more substitution reactions.
  • Suitable precursors include:
  • Such precursors may be reacted with NH2CH2CH2NH2 to provide compounds of the following formulae A1 and A2:
  • a compound of formula A2 maybe prepared by reacting a compound of formula Ai with PH 2 CHNH 2 .
  • a compound of formula A2 may be prepared by first reacting perylene- 3,4,9,10-tetracarboxylic dianhydnde with diphenylaminomethane (Ph 2 CNH 2 ) to afford a compound of formula B3 (see below).
  • Compound B3 is subsequently reacted with diaminoethane (H2NCH2CH2N2) to afford a compound of formula A2.
  • perylen-bis-anhydride may be reacted with a compound of formula 1 to yield a chromophoric compound 2.
  • the commercially available perylen- bis-anhydride in the presence of a Lewis acid and at a temperature between ioo° and 200°C reacts with a substrate containing two amino groups on the same carbon atom, R 2 C(NH 2 ) 2 , to yield a di-chromophoric compound 2.
  • Compound 1 is present in large excess to prevent polymerization.
  • the anhydride functions in 2 can then be converted to imide by reaction with ammonia.
  • the present invention is extremely well exemplified by reference to a particular set of electron acceptor compounds, namely fullerene mimics in combination with P 3 HT as an electron donor compound or other donor compounds having similar electronic energy levels. Consequently, the present invention is further explained below in the context of electron acceptor compounds that mimic fullerene. However, for the avoidance of doubt, the present invention in its broadest terms should not be viewed as limited to the provision of fullerene mimics as described below. It has also been discovered that the formation of an excited electron acceptor anion plays a role in a compound's ability to mimic the photovoltaic properties of fullerene.
  • the vertical excitation energy for an anion can be computed.
  • an efficient acceleration of the charge separation rate is due to the presence of excited states of the anion at 0.22 and 0.44 eV (relative to energy of the neutral).
  • excited states of the anion at energy larger than 0.5 eV are unlikely to contribute to the electron transfer process unless the ground state of the anion is too low, a case of little interest as the system will have large energy losses.
  • the compound exhibits an excited state of its anion at an energy level less than 0.5 eV relative to the energy level of the neutral anion.
  • such compounds preferably comprise at least two unoccupied molecular orbitals having energy levels between about -3.6 eV and -2.2 eV; even more preferably between about - 3.50 eV and -2.60 eV.
  • the chromophore R may be selected from the group consisting of: wherein R' is -H, -NH 2 , -PH 2 or -CF3; wherein R' is -H, -CH 3 , or -NH 2 ;
  • R' is -H or -F
  • R' is -H, or - C 6 H 5 O;
  • the electron acceptor compound is selected from the group consisting of:
  • the compound is selected from the group consisting of:
  • the electron donor compound is preferably poly-(3-hexylthiophene), i.e. P 3 HT.
  • the main characteristics of the fullerene mimics is to have low lying LUMO+i (and possibly LUMO+2 orbital levels) and low lying excited states of the anion. Both properties can be easily computed via quantum chemical methods. The evaluation is also repeated for the [6o]PCBM molecule, which acts as an "internal standard".
  • the energies of the lowest unoccupied orbitals of the 21 newly designed acceptors are reported in Figure 2a (the y axis indicates Energy/ eV) together with the corresponding values for [6o]PCBM, whose LUMO and LUMO+i energy are -3.37 and -3.16 eV respectively.
  • the LUMO energy of the acceptor determines the maximum voltage that can be extracted from a solar cell. Acceptor's LUMO at too low energy compared with the donor's LUMO causes an excessive energy loss. As we are aiming at predicting new possible acceptors to be used in conjunction with P3HT, we can set a minimum acceptable LUMO energy at -3.50 eV.
  • the anion CH 3 R does not have excited states below 0.5 eV while there are respectively one (0.19 eV) and two (0.162, 0.167 eV) low lying excited states of the anion of CH 2 R 2 and CHR 3 .
  • the results are not too different for the series of CH 3 R, CH 2 R 2 , CHR 3 , CR 4 where R is that given in entry 6_i of Table 1.
  • R is that given in entry 6_i of Table 1.
  • the excited state energy of the anion for this series behaves in a more complex way.
  • chromophore R given in entry 5_2 of Table 1 and the separation between the chromophores range from 1 to 10 sp3 carbon atoms.
  • the excitation energy for this series is given in Figure 3 (graph showing lowest excited energy state versus number of carbon atoms). While there is an excited state of the anion of this molecule at low energy, for molecules with more than 3 carbon atoms between the chromophores the excited state is too low in energy (less than 0.03 eV). These molecules behave as two separate chromophores with no acceleration in the charge separation rate. In suitable fullerene mimics the connection between chromophores should not therefore preferably exceed two sp 3 carbon atoms (or the like).
  • Figure 4 reports the same calculation as Figures 2a and 2b but with a restricted number of new acceptors (5_i, 5_2, 5_3, 6_i, 6_2) and the acceptors described in the Sonar review (10a, 48a, 52a, 57, 73b).
  • Figure 4(a) and Figure 4(b) correspond to Figure 2(a) and 2(b) respectively.
  • Figures 4(c) and 4(d) replicate the information of 4(a) and 4(b) with a different range of energy.
  • Figure 4 reports the energy of the unoccupied orbitals (left) and lowest excited state energy of anion (right) of already known non-fullerene acceptors and designed acceptors at B3LYP/6-31G* level. Top and bottom panels differ with respect to the range of energies. The percent figure in panel 4(a) is the experimental efficiency of the cell.
  • PDA perylene-3,4,9,io-tetracarboxylic acid dianhydride
  • PDA is first transformed in 3,4,9,io-tetracarboxylic-3,4-anhydride-9,io- imide 1.
  • PDA (2.0 mmol) was suspendedn in quinoline, and then Zn(AcO) 2 (0.2 mmol) and diphenylmetanamine (0,4 mmol) were added. The mixture was heated at i8o°C until the disappearance of the amine (6 h). To the solution brought at room
  • 1 and 2 can be separated chromatographically as detailed in the experimental section.
  • the mixture of 1 and 2 can be further reacted by addition of etylendiamina (0.4 mmol) e Zn(AcO) 2 (0.2 mmol) and heated overnight at i8o°C.
  • the solution is brought to room temperature and worked as described in the experimental section to obtain pure 3.
  • a remarkable feature of the ⁇ - ⁇ 3 is the presence of a multiplet for the fragment CH 2 -CH 2 (in agreement with the present of a system aa'xx').
  • diphenylmetanamine (3.0 mmol, 500 mg) were added.
  • the mixture is heated at i8o°C for 5-6 hours.
  • Second procedure to a suspension of perylene-3,4,9,io-tetracarboxylic acid dianhydride (2.0 mmol, 770 mg) in 8 ml of quinoline, under N 2 flux and magnetic stirring Zn(AcO) 2 (0.2 mmol, 35 mg) and etylendiamina (0.5 mmol, 30 mg) were added.
  • the mixture was heated for 6 h at i8o°C and then, diphenylmetanamine (3.0 mmol, 500 mg) was added. Heating was maintained at the same temperature overnight.
  • the signal of the monoanionic species display new bands that cannot be due to any molecular vibrations at 2600 and 2300 cm 1 (the latter is close to the spurion silicon adsorption due to the instrumentation). These signals can be only attributed to very low electronic transition of the monoanion as predicted by the theory.

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Abstract

La présente invention concerne des composés organiques accepteurs d'électrons, et ces derniers combinés à un composé donneur d'électrons, ainsi que des matériaux et des dispositifs électroniques les comprenant. L'invention concerne également l'utilisation de composés organiques accepteurs d'électrons dans des cellules photovoltaïques ainsi que la préparation de tels composés.
PCT/GB2013/051484 2012-06-06 2013-06-05 Composés organiques accepteurs d'électrons WO2013182847A1 (fr)

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US11678569B2 (en) 2020-03-31 2023-06-13 Idemitsu Kosan Co., Ltd. Compound, material for organic electroluminescent elements, organic electroluminescent element, and electronic device

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