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WO 2017/063026 Al 20 April 2017 (20.04.2017) P O P CT (12) INTERNATIONAL APPLICATION PUBLISHED UNDER THE PATENT COOPERATION TREATY (PCT) (19) World Intellectual Property Organization I International Bureau (10) International Publication Number (43) International Publication Date WO 2017/063026 Al 20 April 2017 (20.04.2017) P O P CT (51) International Patent Classification: (81) Designated States (unless otherwise indicated, for every B01F 3/12 (2006.01) B82Y 30/00 (201 1.01) kind of national protection available): AE, AG, AL, AM, C01B 31/02 (2006.01) B82Y 40/00 (201 1.01) AO, AT, AU, AZ, BA, BB, BG, BH, BN, BR, BW, BY, B01J 19/10 (2006.01) H01B 1/20 (2006.01) BZ, CA, CH, CL, CN, CO, CR, CU, CZ, DE, DJ, DK, DM, DO, DZ, EC, EE, EG, ES, FI, GB, GD, GE, GH, GM, GT, (21) International Application Number: HN, HR, HU, ID, IL, IN, IR, IS, JP, KE, KG, KN, KP, KR, PCT/AU2016/000354 KW, KZ, LA, LC, LK, LR, LS, LU, LY, MA, MD, ME, (22) International Filing Date: MG, MK, MN, MW, MX, MY, MZ, NA, NG, NI, NO, NZ, 14 October 2016 (14.10.201 6) OM, PA, PE, PG, PH, PL, PT, QA, RO, RS, RU, RW, SA, SC, SD, SE, SG, SK, SL, SM, ST, SV, SY, TH, TJ, TM, (25) Filing Language: English TN, TR, TT, TZ, UA, UG, US, UZ, VC, VN, ZA, ZM, (26) Publication Language: English ZW. (30) Priority Data: (84) Designated States (unless otherwise indicated, for every 20155904218 15 October 2015 (15. 10.2015) AU kind of regional protection available): ARIPO (BW, GH, GM, KE, LR, LS, MW, MZ, NA, RW, SD, SL, ST, SZ, (71) Applicant: THE AUSTRALIAN NATIONAL UNIVER¬ TZ, UG, ZM, ZW), Eurasian (AM, AZ, BY, KG, KZ, RU, SITY [AU/AU]; Acton, ACT 2601 (AU). TJ, TM), European (AL, AT, BE, BG, CH, CY, CZ, DE, DK, EE, ES, FI, FR, GB, GR, HR, HU, IE, IS, IT, LT, LU, (72) Inventors: NOTLEY, Shannon Marc; 7 Low Place, LV, MC, MK, MT, NL, NO, PL, PT, RO, RS, SE, SI, SK, Pearce, ACT 2607 (AU). GHARIB, Desi Hamed; 9/69 SM, TR), OAPI (BF, BJ, CF, CG, CI, CM, GA, GN, GQ, Auburn Road, Hawthorn, VIC 3 122 (AU). GW, KM, ML, MR, NE, SN, TD, TG). (74) Agent: SPRUSON & FERGUSON; GPO Box 3898, Published: Sydney, NSW 2001 (AU). — with international search report (Art. 21(3)) o © o- (54) Title: DISPERSIONS (57) Abstract: The invention relates to a method for producing a dispersion of molecular layers in an organic liquid. The method comprises combining an agglomerate of said molecular layers with an electron-deficient aromatic compound; before or after step a) combining the agglomerate network with the organic liquid; and, after step a), providing mechamcal energy to the agglomerate so as to produce a dispersion of the molecular layers in the organic liquid. DISPERSIONS Field [0001] This specification relates to exfoliation of agglomerated materials so as to produce a dispersion of discrete molecular layers. Priority [0002] This application claims priority from Australian Provisional Patent Application No. 2015904218, the entire contents of which are incorporated herein by cross-reference. Background [0003] Various substances which are composed of extended benzenoid structures have recently attracted a great deal of attention due in part to their thermal and electrical properties. A well- known example of such materials is graphene, the exfoliated form of graphite. Another example is carbon nanotubes, which may be regarded as cylinders of graphene-like material. These may be single walled (SWCNT) or multiwalled (MWCNT). Other examples include carbon whiskers, fullerenes and carbon fibres. Certain inorganic materials, such as molybdenum sulfide, are also known to have a graphite-like layered structure, and it is known that such materials can be separated into their deagglomerated layers. In this specification the term "molecular layer" will be used to encompass materials as set out above having extended benzenoid sheets (either flat, as in graphene, cylindrical as in carbon nanotubes, or in any other form) as well as inorganic materials in the form of extended sheets, and the term "agglomerated molecular layer" will be used to refer to the agglomerated form of such materials (i.e. graphite, agglomerated nanotubes etc.). [0004] One problem with manipulation of these materials is their tendency to agglomerate, driven by the energetic benefit of extensive van der Waals forces, specifically π-π interactions. Thus graphene can agglomerate to form a graphite-like material, and indeed occurs naturally as graphite, which may be viewed as agglomerated graphene sheets. Similarly, carbon nanotubes can agglomerate to form ropes, bundles or aggregates. [0005] Charge transfer (CT) interactions are intermolecular interactions between π electron rich (donor) and π electron deficient (acceptor) molecules. CT interaction can be effectively used to cleave and interrupt π- π interactions between molecular layers resulting in deaggregation. The resulting CT complex shows a characteristic absorption band in the visible region providing evidence of association. For this to be realized, the design and strength of the electron acceptors is important. This is because the breaking of π- π interaction has energetic consequences. Weak electron acceptors or donors such as fullerene (C o) do not match the energetic cost associated with such cleavage and hence are poor CT additives. [0006] Graphene is a two dimensional crystalline nanomaterial that consists of a single atomic layer of carbon bonded together in a hexagonal lattice. The term "graphene" is also used to refer to small numbers, e.g. less than about 10, of such layers which are laminated together. Graphene has attracted a great deal attention due to its extraordinary physical and chemical properties. Recently, research has been geared towards increasing the quality and yield of graphene exfoliation so as to ensure practical applications in various areas. Direct liquid phase exfoliation of graphite powder in a well-chosen organic solvent has the potential to produce materials for use in applications such as functional coatings, conducting inks, composite, batteries, supercapacitors and top down approaches to electronics. In this method, solvents that have matching surface energies with graphene, such as N -methylpyrrolidone (NMP) or dimethylformamide (DMF), can be directly used to exfoliate graphite through simple sonication. [0007] However, this method has a significant disadvantage in that the yield is very low, typically 0.01 mg/mL of exfoliated graphene, and improving the yield requires very long sonication times which is often impractical for large scale applications. Furthermore, the process is limited to solvents with a well matched surface energy, which are often either too expensive or have high boiling points rendering further processing impractical or of limited utility. [0008] Extending liquid phase exfoliation of graphene to lower boiling point, non-polar solvents such as chloroform, which have relatively poor matching surface energy, would thus be advantageous in increasing the range of solvents available for many graphene applications such as preparation of polymer-graphene composites, since many commodity polymers are soluble in these solvents. Also, reducing the sonication time would be advantageous, since extended sonication times can cause rupture of graphene sheets, leading to a poor quality product with small sheets. [0009] Moreover, since the best solvent that is currently known for liquid phase exfoliation of graphene in organic solvent is NMP, a solvent that is currently on the European candidate list of substances of high concern due to its toxicity, it would be beneficial to identify alternative, greener solvents for graphene exfoliation so as to meet environmental and safety standards. In addition to exfoliation in greener organic solvents, eliminating the need for solvents all together during composite formation would not only be highly attractive from an environmental conservation perspective but would also greatly reduce the processing costs associated with highly priced solvents. [00010] There is also a need, in certain applications, to modify the electrical properties of graphene. The zero gap characteristic of pristine graphene, with attendant difficulty in development of a bulk non-covalent approach to both open and tune the band gap without destroying the sp2 graphene basal planes, has also limited its applications in electronic devices. For instance, graphene based transistors have been considered as a potential substitute for the conventional silicon semiconductor-based microelectronics. This is due to the fact that modern logic circuits are based on silicon complementary metal oxide semiconductor (CMOS) technology. Thus, band gap tuning and exploring the electronic properties of graphene is of fundamental importance for many applications, especially in field effect transistors (FETs) where both p-type and n-type conductions are desired to construct complex logic circuits. Solution processing of bulk non- covalently doped graphene without the need of special equipment would open up additional potential of low cost method for fabrication of semiconductor and electronic devices. [0001 1] It is an aim of the present invention to at least partially overcome at least one of the above disadvantages of previous methods and products. It is a further aim to at least partially satisfy at least one of the above needs. Summary of Invention [00012] In a first aspect of the invention there is provided a method for producing a dispersion of molecular layers in an organic liquid, said method comprising: a) combining an agglomerate of said molecular layers with an electron-deficient aromatic compound; b) before or after step a), combining said agglomerate with the organic liquid; and c) after step a), providing mechanical energy to said agglomerate so as to separate said agglomerate into molecular layers. [00013] The agglomerate of molecular layers may be graphite or it may be aggregated carbon nanotubes or it may be an inorganic layer material such as the transition metal dichalcogenide molybdenum disulfide or it may be a mixture of these.
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