Polyfluoroaromatic derivatives for liquid lenses

Abstract

A liquid lens includes a first liquid including a polyfluorinated aromatic compound represented by formula (I): Fx-(aromatic)-Y-R1. And x is in the range of 2 to 5. Y is one of CH2, Si (Alk) 2, Ge (Alk) 2, O and S. 'Alk' is a linear aliphatic chain. R1 is any organic group, but can be one of a linear aliphatic chain, alicyclic, fluoroalicyclic, and aromatic residues. "Aromatic" is any six-carbon aromatic ring. Examples of chemical compounds represented by Formula (I) include butylpentafluorobenzene; the solvent is dimethyl nonafluorohexyl pentafluorophenyl silane; and trimethyl pentafluorophenyl germane; butoxy pentafluorobenzene is used as a raw material; cyclopentyloxy pentafluorobenzene is used as a raw material; the catalyst is 1, 1-n-octyloxy pentafluorobenzene; 2, cyclooctyloxy pentafluorobenzene; the catalyst is 1, 1-n-dodecyloxy pentafluorobenzene; adding cyclopentyl pentafluorophenyl sulfide; a phenoxy pentafluorobenzene group; 2, 2, 4-difluoroanisole and heptafluoropentyloxy pentafluorobenzene are used as raw materials. The density of the first liquid is in the range of 0.95 g / mL to 1.35 g / mL (at 20 DEG C). The liquid further includes a second liquid that forms an interface with the first liquid. The second liquid may be substantially free of water.

Description

[0001] This application claims the benefit of priority under 35 U.S.C. §120 to U.S. Provisional Application Serial No. 63 / 397,417, filed on August 12, 2022, the contents of which are hereby based upon and incorporated herein by reference in their entirety. Technical Field

[0002] The present disclosure relates generally to liquid lenses based on electrowetting, and more particularly to non-conductive liquids containing polyfluorinated aromatic compounds for use in liquid lenses. Background Art

[0003] Transmissive liquid lenses generally enclose two immiscible liquids within a body or shell, one of which is a polar liquid, also known as a conductive liquid, and one of which is a non-conductive liquid, also known as an insulating and / or non-polar liquid. The shell contains electrodes through which the shape of the interface between the two immiscible liquids can be manipulated based on the principle of electrowetting. Typically, the two liquids have approximately the same density but different refractive indices.

[0004] Typically, non-conductive liquids are mixtures of several substances, since a single substance alone does not have the desired combination of properties, such as density or refractive index. To date, organogermane compounds and perfluoroalkanes have been used as components of non-conductive liquids. However, these substances present problems. For example, organogermane compounds are relatively expensive, which increases the cost of the liquid lens. In addition, perfluoroalkanes have limited miscibility with other substances that might be desired to form a non-liquid lens with the desired properties. Summary of the invention

[0005] The present disclosure solves the above problems by using a non-conductive liquid, wherein the non-conductive liquid includes a polyfluoro aromatic compound represented by the following formula (I): (I) F x —(Aromatic)—Y—R1 wherein x is in the range of 2 to 5; wherein Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "Alk" is a linear aliphatic chain, wherein R1 is any organic group, and wherein "aromatic" is any six-carbon aromatic ring. The polyfluoroaromatic compound of formula (I) above can be formulated relatively cheaply, has an adjustable density and refractive index, has a desired miscibility with other desired substances that can form a non-conductive liquid, has an adjustable immiscibility with a conductive liquid, and has high hydrolytic stability.

[0006] According to the first aspect of the present disclosure, a liquid lens comprises: a first liquid comprising a polyfluoro aromatic compound represented by formula (I): (I) F x—(Aromatic)—Y—R1 wherein x is in the range of 2 to 5; wherein Y is any organic or inorganic moiety; wherein R1 is any organic group, and "aromatic" is any six-carbon aromatic ring; wherein the liquid lens exhibits a hysteresis increase of 1 diopter or less from the initial hysteresis after storage at 85°C for at least 120 hours.

[0007] According to the second aspect of the present disclosure, there is provided the liquid lens of the first aspect, wherein Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "Alk" is a linear aliphatic chain.

[0008] According to a third aspect of the present disclosure, there is provided the liquid lens of any one of aspects 1 to 2, wherein R1 is selected from a linear aliphatic chain, an alicyclic, a fluorinated alicyclic and an aromatic residue.

[0009] According to the fourth aspect of the present disclosure, a liquid lens according to any one of aspects 1 to 3 is provided, wherein F of formula (I) x The (aromatic) part is a fluorinated benzene ring.

[0010] According to the fifth aspect of the present disclosure, a liquid lens according to any one of the first to third aspects is provided, wherein F of formula (I) x The (aromatic) moiety is a pentafluorobenzene ring containing five fluorine substituents.

[0011] According to the sixth aspect of the present disclosure, there is provided the liquid lens of the first aspect, wherein the polyfluoro aromatic compound is represented by the following formula (II): wherein x is in the range of 2 to 5; wherein Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "alk" is a linear aliphatic chain; and wherein R1 is selected from a linear aliphatic chain, alicyclic, fluoroalicyclic and aromatic residues.

[0012] According to the seventh aspect of the present disclosure, there is provided the liquid lens of the first aspect, wherein the polyfluoro aromatic compound is represented by the following formula (III): wherein x is in the range of 2 to 4; wherein Y is any organic or inorganic moiety; wherein R1 is any organic group; and wherein R2 is any organic group.

[0013] According to the 8th aspect of the present disclosure, the liquid lens of any one of aspects 1 to 7 also includes a second liquid, wherein the first liquid and the second liquid (i) form an interface between the first liquid and the second liquid, and (ii) comprise a miscibility of less than 2% in the temperature range of -30°C to 85°C; and wherein the first liquid comprises a density of 0.95 g / mL to 1.35 g / mL (at 20°C).

[0014] According to a ninth aspect of the present disclosure, there is provided the liquid lens of the eighth aspect, wherein the second liquid does not substantially contain water.

[0015] According to the tenth aspect of the present disclosure, a liquid lens includes: (a) a first liquid containing a polyfluoro aromatic compound represented by the following formula (I): (I) F x —(Aromatic)—Y—R1 wherein x is in the range of 2 to 5; wherein Y1 is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "Alk" is a linear aliphatic chain, wherein R is any organic group, and "aromatic" is any six-carbon aromatic ring; and (b) a second liquid, wherein the first liquid and the second liquid (i) form an interface between the first liquid and the second liquid, and (ii) comprise a miscibility of less than 2% over a temperature range of -30°C to 85°C; and (iii) each comprise a density, the density difference being less than 0.1 g / mL.

[0016] According to the 11th aspect of the present disclosure, there is provided the liquid lens of the 10th aspect, wherein R1 is selected from the group consisting of linear aliphatic chain, alicyclic, fluoroalicyclic and aromatic residues.

[0017] According to the 12th aspect of the present disclosure, a liquid lens according to any one of aspects 1 to 11 is provided, wherein F of formula (I) x The (aromatic) part is a fluorinated benzene ring.

[0018] According to the 13th aspect of the present disclosure, a liquid lens according to any one of aspects 10 to 11 is provided, wherein F of formula (I) x The (aromatic) moiety is a pentafluorobenzene ring containing five fluorine substituents.

[0019] According to the 14th aspect of the present disclosure, there is provided the liquid lens of the 10th aspect, wherein the polyfluoro aromatic compound is represented by the following formula (II): wherein x is in the range of 2 to 5; wherein Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "alk" is a linear aliphatic chain; and wherein R1 is selected from a linear aliphatic chain, alicyclic, fluoroalicyclic and aromatic residues.

[0020] According to the 15th aspect of the present disclosure, there is provided a liquid lens according to any one of aspects 10 and 14, wherein the polyfluoro aromatic compound is selected from the following group: Butylpentafluorobenzene; Dimethylnonafluorohexylpentafluorophenylsilane; Trimethylpentafluorophenylgermane; Butoxypentafluorobenzene; Cyclopentyloxypentafluorobenzene; 1-n-octyloxypentafluorobenzene; Cyclooctyloxypentafluorobenzene; 1-n-Dodecyloxypentafluorobenzene; Cyclopentyl pentafluorophenyl sulfide; Phenoxypentafluorobenzene; 2,4-Difluoroanisole; and Heptafluoropentyloxypentafluorobenzene.

[0021] According to the 16th aspect of the present disclosure, there is provided the liquid lens of the 10th aspect, wherein the polyfluoro aromatic compound is represented by the following formula (III): wherein x is in the range of 2 to 4; wherein Y is any organic or inorganic moiety; wherein R1 is any organic group; and wherein R2 is any organic group.

[0022] According to the 17th aspect of the present disclosure, a liquid lens according to any one of aspects 10 to 16 is provided, wherein (i) the first liquid comprises a density (at 20° C.) in the range of 0.95 g / mL to 1.35 g / mL; and (ii) the second liquid is water-based, glycol-based or ionic liquid-based.

[0023] According to an eighteenth aspect of the present disclosure, there is provided the liquid lens of any one of aspects 10 to 16, wherein the second liquid is substantially free of water.

[0024] According to the 19th aspect of the present disclosure, a method for manufacturing a liquid lens comprises: (A) providing a first liquid in a substrate, wherein the first liquid comprises a polyfluoro aromatic compound represented by the following formula (I): (I) F x —(Aromatic)—Y—R1 wherein x is in the range of 2 to 5; wherein Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "Alk" is a linear aliphatic chain; wherein R1 is any organic group, and "aromatic" is any six-carbon aromatic ring; and (B) a second liquid is disposed in the substrate, wherein (a) the first liquid and the second liquid (i) form an interface between the first liquid and the second liquid, and (ii) comprise a miscibility of less than 2% in the temperature range of -30°C to 85°C, (b) the first liquid comprises a density of 0.95 g / mL to 1.35 g / mL (at 20°C), (c) the difference between the density of the first liquid and the density of the second liquid is less than 0.1 g / mL, and (d) the difference between the refractive index of the first liquid and the refractive index of the second liquid is in the range of 0.02 to 0.24.

[0025] According to the 20th aspect of the present disclosure, the method of the 19th aspect is provided, wherein (a) F of formula (I) x - the (aromatic) moiety is a fluorinated benzene ring, and (b) the second liquid is substantially free of water.

[0026] According to the 21st aspect of the present disclosure, there is provided a liquid lens according to any one of aspects 1, 6, 8 and 9, wherein the polyfluoro aromatic compound is selected from the group consisting of: Butylpentafluorobenzene; Dimethylnonafluorohexylpentafluorophenylsilane; Trimethylpentafluorophenylgermane; Butoxypentafluorobenzene; Cyclopentyloxypentafluorobenzene; 1-n-octyloxypentafluorobenzene; Cyclooctyloxypentafluorobenzene; 1-n-Dodecyloxypentafluorobenzene; Cyclopentyl pentafluorophenyl sulfide; Phenoxypentafluorobenzene; 2,4-Difluoroanisole; and Heptafluoropentyloxypentafluorobenzene.

[0027] According to the 22nd aspect of the present disclosure, there is provided a method according to any one of aspects 19 to 20, wherein the polyfluoro aromatic compound is selected from the group consisting of: Butylpentafluorobenzene; Dimethylnonafluorohexylpentafluorophenylsilane; Trimethylpentafluorophenylgermane; Butoxypentafluorobenzene; Cyclopentyloxypentafluorobenzene; 1-n-octyloxypentafluorobenzene; Cyclooctyloxypentafluorobenzene; 1-n-Dodecyloxypentafluorobenzene; Cyclopentyl pentafluorophenyl sulfide; Phenoxypentafluorobenzene; 2,4-Difluoroanisole; and Heptafluoropentyloxypentafluorobenzene.

[0028] Other features and advantages are given in the following detailed description, some of which are readily apparent to those skilled in the art from the description or recognized by practicing the various embodiments described herein, including the following detailed description, claims, and drawings.

[0029] It should be understood that the foregoing general description and the following detailed description are merely exemplary and are intended to provide an overall review or framework for understanding the nature and characteristics of the claims. The included drawings provide further understanding and are incorporated into and constitute a part of this specification. The drawings illustrate one or more embodiments and, together with the description, are used to explain the principles and operations of the various embodiments. BRIEF DESCRIPTION OF THE DRAWINGS

[0030] In the attached picture:

[0031] Figure 1 is a schematic cross-sectional view of a liquid lens embodiment according to various embodiments of the present disclosure, illustrating a first liquid and a second liquid separated by an interface; and

[0032] Figure 2 is to make liquid lenses, e.g. Figure 1 Flowchart of the liquid lens method. DETAILED DESCRIPTION

[0033] The preferred embodiments are described in detail below, examples of which are shown in the accompanying drawings. Whenever possible, the same reference numerals will be used throughout the drawings to refer to the same or similar parts.

[0034] It should be understood that the present disclosure may take the form of alternative Figure 1 and Figure 2 The various orientations and step orders shown in the drawings and step orders are not limited to the various orientations and step orders, unless explicitly stated to the contrary. It should also be understood that the specific disclosures illustrated in the drawings and described in the following description are merely exemplary embodiments of the inventive concepts defined in the appended claims. Therefore, the specific dimensions and other physical characteristics associated with the embodiments disclosed herein should not be understood as limiting unless otherwise explicitly stated in the claims.

[0035] Liquid lens 10

[0036] Reference now Figure 1In an embodiment, the liquid lens 10 includes a substrate 12 and a cover 14. The substrate 12 and the cover 14 can be mounted relative to each other to facilitate maintaining a fluid-tight containment region 16, thereby providing electrical insulation between the substrate 12 and the cover 14. A gasket 18 can be disposed between the substrate 12 and the cover 14 to facilitate maintaining the fluid-tight containment region 16.

[0037] The liquid lens 10 includes a first electrode 20, an optical axis 22, and a second electrode 24. In an embodiment, the liquid lens 10 is rotationally symmetric about the optical axis 22. The first electrode 20 and / or the second electrode 24 may include a conductor. In an embodiment, the first electrode 20 and / or the second electrode 24 include a metal, such as one or more of copper, silver, gold, platinum, aluminum, chromium, titanium, nickel, steel, bronze, and / or brass. In an embodiment, the first electrode 20 and / or the second electrode 24 include a conductive polymer, such as one or more of the following: poly(3,4,-ethylenedioxythiophene) (PEDOT), polyphenylene sulfide (PSS), PEDOT:PSS, polyparaphenylene (PpP), polythiophene (PTh), polyaniline (PANI), polypyrrole (PPy), polyphthalocyanine (PPhc), or polyisothionaphthalene (PITN). In an embodiment, the first electrode 20 and / or the second electrode 24 include a material that is transparent in the desired operating wavelength range of the liquid lens 10. In an embodiment, the second electrode 24 comprises one or more of PEDOT, PEDOT:PSS, aluminum oxide, cadmium oxide, gallium oxide, tin oxide (e.g., indium tin oxide (ITO)), and zinc oxide. In an embodiment, the first electrode 20 and / or the second electrode 24 are doped with one or more transition metals and / or Group IIIA metals (e.g., aluminum, gallium, indium, thallium). In an embodiment, the first electrode 20 and / or the second electrode 24 comprise an intrinsically conductive polymer (e.g., the polymer bulk is conductive). In an embodiment, the first electrode 20 and / or the second electrode 24 comprise a polymer composite with nanoparticles and / or carbon fibers.

[0038] In an embodiment, the first electrode 20 surrounds the first window 26 through the through hole 28. In an embodiment, the first window 26 further includes a first substrate 30. In an embodiment, the first substrate 30 is installed relative to the through hole 28. In an embodiment, the first substrate 30 is completely installed in the through hole 28 of the first electrode 20, and the first electrode 20 completely surrounds the first substrate 30.

[0039] In an embodiment, the second electrode 24 at least partially surrounds the second window 32 through a through hole 34 of the second electrode 24. In an embodiment, the through hole 34 of the second electrode 24 has a cross-sectional diameter in a direction perpendicular to the optical axis 22, and the cross-sectional diameter is stepped to define a base 35. In an embodiment, the second window 32 further includes a second substrate 36. In an embodiment, the second substrate 36 is installed relative to the corresponding through hole 34. In an embodiment, a portion 38 of the second electrode 24 extends on a peripheral portion of one or both major surfaces of the second substrate 36.

[0040] In an embodiment, the second substrate 36 is mounted to the base 35 of the through hole 34 by a fitting 40. Additionally, in an embodiment, the substrate 12 includes the second electrode 24, the second window 32, and the fitting 40. In such an embodiment, the gasket 18 provides a fluid seal between the second electrode 24 of the substrate 12 and the cover 14 to facilitate maintaining the fluid-tight containment area 16.

[0041] In an embodiment, the cover 14 includes or supports the first electrode 20 and the first window 26. In an embodiment, the cover 14 defines an effective through hole 42 that is smaller than the diameter of the through hole 28 of the first electrode 20, wherein a lip 44 extends over the outer surface of the first electrode 20 and the peripheral portion of the first window 26 to protect the first electrode 20 and the interface between the first substrate 30 and the first electrode 20 from external forces and environmental conditions. In addition, the lip 44 extends over the outer peripheral surface of the first electrode 20 to further help protect the first electrode 20 from external forces and environmental conditions, and to help position the first electrode 20 in the receiving area of ​​the cover 14. In an embodiment, the cover 14 has a shape that is rotationally symmetrical about the optical axis 22. In an embodiment, as shown in the figure, the cover 14 has a substantially "S"-shaped portion 46, which has a curved portion, wherein one curved portion has an opening facing the fluid-tight receiving area 16, and the other curved portion has an opening facing away from the fluid-tight receiving area 16. The substantially “S”-shaped portion 46 may allow the first substrate 30a to move somewhat along the optical axis 22 when pressure is applied by the fluid within the fluid-tight containing area 16 of the liquid lens 10 (described further below) and / or when pressure is applied to the cover 14 of the liquid lens 10 from the outside.

[0042] The optical axis 22 intersects both the first window 26 and the second window 32. In an embodiment, as shown, the optical axis 22 passes through the volumetric center of both the first substrate 30 and the second substrate 36. In an embodiment, the second window 32 is aligned with the first window 26 along the optical axis 22.

[0043] In an embodiment, the transmittance of incident electromagnetic radiation 47 of a desired wavelength range entering or exiting the fluid-tight containment area 16 through the first window 26 and the second window 32 is about 85% or greater. In an embodiment, the first substrate 30 and the second substrate 36 each have an average transmittance of about 85% or greater, about 88% or greater, about 90% or greater, about 92% or greater, about 94% or greater, about 96% or greater, about 98% or greater, or about 99% or greater over the operating wavelength range of the incident electromagnetic radiation 46. As used herein, "transmittance" refers to the arithmetic average (e.g., mean) percentage of the incident intensity of electromagnetic radiation 46 transmitted through a material or device over the operating wavelength range. In an embodiment, the operating wavelength range can be within the visible optical wavelength. In embodiments, the operating wavelength range may be within a wavelength range of about 400 nanometers (nm) to 700 nm, about 400 nm to about 550 nm, about 550 nm to about 700 nm, about 600 nm to about 700 nm, or any range or sub-range therebetween. In some embodiments, the operating wavelength range may include infrared wavelengths, for example, including a wavelength range of about 700 nm to about 1,000 micrometers (μm). In embodiments, the operating wavelength range may be within an ultraviolet wavelength range, for example, including a wavelength range of about 10 nm to about 400 nm.

[0044] The first substrate 30 and / or the second substrate 36 may include a polymer, a crystalline material (e.g., quartz, sapphire, single or polycrystalline alumina, spinel (MgAl2O4)), a glass-based material, or a combination thereof. Examples of suitable polymers include, but are not limited to, copolymers and blends thereof comprising: thermoplastic materials, including polystyrene (PS), polycarbonate (PC); polyesters, including polyethylene terephthalate (PET); polyolefins, including polyethylene (PE); acrylic polymers, including polymethyl methacrylate (PMMA); epoxies; and silicones, including polydimethylsiloxane (PDMS). As used herein, "glass-based" includes both glass and glass-ceramics, wherein the glass-ceramics have one or more crystalline phases and an amorphous residual glass phase. Glass-based materials may include amorphous materials (e.g., glass) and optionally one or more crystalline materials (e.g., ceramics). Exemplary glass-based materials that may or may not contain lithium oxide include soda-lime glass, alkali aluminosilicate glass, alkali-containing borosilicate glass, alkali aluminophosphosilicate glass, and alkali aluminoborosilicate glass.

[0045] The liquid lens 10 also includes a first liquid 48 and a second liquid 50 disposed within the fluid-tight containing area 16. An interface 52 is formed between the first liquid 48 and the second liquid 50. For example, in an embodiment, the first liquid 48 and the second liquid 50 are immiscible. The terms "non-miscible" and "immiscible" as used herein refer to liquids that do not form a uniform mixture when added together, or that mix very little when one liquid is added to another liquid. In some instances, the two liquids are considered to be immiscible when the partial miscibility of the two liquids is less than 2%, less than 1%, less than 0.5%, or less than 0.2%, all values ​​being measured within a given temperature range (e.g., at 20°C). Low mutual miscibility may be preferred over an exemplary temperature range of -30°C to 85°C, or -20°C to 65°C.

[0046] Although not shown, in embodiments, the interface 52 may be a transparent film that separates the first liquid 48 from the second liquid 50. Regardless, the interface 52 forms a lens. In embodiments, the first liquid 48 and the second liquid 50 have substantially the same density, which may help prevent the shape of the interface 52 from changing due to a change in the physical orientation of the liquid lens 10 (e.g., due to gravity). Thus, in some examples, the difference between the density of the first liquid 48 and the density of the second liquid 50 is less than 0.1 g / mL (e.g., in the range of 0.00 g / mL to 0.09 g / mL).

[0047] In an embodiment, the refractive index of the first liquid 48 is greater than the refractive index of the second liquid 50. In an embodiment, the refractive index of the first liquid 48 is less than the refractive index of the second liquid 50. In an embodiment, the difference between the refractive index of the first liquid 48 and the refractive index of the second liquid 50 is in a range of 0.02 to 0.24. The optical axis 22 passes through the interface 52.

[0048] In an embodiment, the second liquid 50 is a conductive liquid. In an embodiment, the second liquid 50 is a polar liquid. In an embodiment, the second liquid 50 is water-based, glycol-based, or ionic liquid-based. Examples of suitable liquids for the second liquid 50 include alcohols (e.g., methanol, propylene glycol), glycols (e.g., ethylene glycol, propylene glycol, trimethylene glycol), ionic liquids (e.g., lithium carbonate, 1-ethyl-3-methylimidazolium-based liquids, 1-alkylpyridinium-based liquids, 1-butyl-3-methylimidazolium tetrafluoroborate-based liquids, N-methyl-N-alkylpyrrolidinium-based liquids), inorganic ionic solutions (e.g., sodium phosphate, sodium bromide, sodium chloride, calcium chloride, lithium chloride, ammonium carbonate, ammonium tetrafluoroborate, potassium nitrate), organic ionic solutions (e.g., potassium acetate, acetic acid, succinic acid, iminodiacetic acid (IDA), Nitrilotriacetic acid (NTA), ethylenediaminetetraacetic acid (EDTA), diethylenetriaminepentaacetic acid (DTPA), ethylene glycoltetraacetic acid (EGTA), 1,2-bis(o-aminophenoxy)ethane-N,N,-N'N'-tetraacetic acid (BAPTA), 2,2'2"-(1,4,7,-triazacyclononane-1,4,7-triyl)triacetic acid (NOTA), 1,4,7,10-tetraazacyclododecane-1,4,7,10-tetraacetic acid (DOTA), and combinations thereof (e.g., 0.1 w / w potassium acetate in ethylene glycol). As used herein, the term "conductive liquid" refers to a liquid having a conductivity of about 1×10 -3 Siemens / meter (S / m) to about 1×10 2 S / m, about 0.1 S / m to about 10 S / m, or about 0.1 S / m to about 1 S / m. In an embodiment, the second liquid 50 is substantially free of water, which means that water is not intentionally present in the second liquid 50, and if unintentionally present, water accounts for less than 0.1% by weight of the second liquid.

[0049] In an embodiment, the density of the second liquid 50 is 0.95 g / mL, 1.00 g / mL, 1.05 g / mL, 1.10 g / mL, 1.15 g / mL, 1.20 g / mL, 1.25 g / mL, 1.30 g / mL, or 1.35 g / mL, or within any range bounded by any two of these values ​​(e.g., 0.95 g / mL to 1.35 g / mL, 1.10 g / mL to 1.30 g / mL, etc.).

[0050] The liquid lens 10 further includes an insulating layer 54. The insulating layer 54 covers the second window 32, the through hole 34, and the second electrode 24 from the perspective of the receiving area 16. The insulating layer 54 covers the portion of the second substrate 36 that is not covered by the second electrode 24. The insulating layer 54 has a thickness 56. In an embodiment, the thickness of the insulating layer 54 varies depending on the distance from the optical axis 22. The first electrode 20 is electrically connected to the second liquid 50. The insulating layer 54 insulates the first liquid 48 and the second liquid 50 from the second electrode 24. In an embodiment, the insulating layer 54 is sufficiently transparent to allow the electromagnetic radiation 46 desired to be sensed to pass through the second window 32 described herein.

[0051] In an embodiment, the containment region 16 includes a first portion 58 (or base portion) and a second portion 60 (or headspace). In an embodiment, at least a portion of the first liquid 48 is disposed within the first portion 58 of the containment region 16, and at least a portion of the second liquid 50 is disposed within the second portion 60 of the containment region 16. In an embodiment, substantially all of the first liquid 48 is disposed within the first portion 58 of the containment region 16. In an embodiment, a perimeter 62 of the interface 52 (e.g., an edge of the interface that contacts the insulating layer 54) is disposed within the first portion 58 of the containment region 16.

[0052] In an embodiment, the receiving area 16 (e.g., the first portion 58 of the receiving area 16) is as follows Figure 1 The receiving area 16 is tapered so that the cross-sectional area of ​​the receiving area 16 decreases along the optical axis 22 in the direction from the first window 26 to the second window 32. For example, the first portion 58 of the receiving area 16 includes a narrow end 64 and a wide end 66. The terms "narrow" and "wide" are relative terms, meaning that the narrow end 64 is narrower than the wide end 66, or has a smaller width or diameter than the wide end 66. Such a tapered receiving area 16 can help the interface 52 between the first liquid 58 and the second liquid 50 to maintain alignment along the optical axis 22. In other embodiments, the receiving area 16 is tapered so that the cross-sectional area of ​​the receiving area 16 increases along the optical axis 22 in the direction from the first window 26 to the second window 32, or the receiving area 16 is not tapered so that the cross-sectional area of ​​the receiving area 16 remains substantially constant along the optical axis 22.

[0053] In an embodiment, electromagnetic radiation 47 (e.g., one or more of visible light, ultraviolet light, and infrared radiation) enters the liquid lens 10 through the first window 26, is refracted at the interface 52 between the first liquid 48 and the second liquid 50, and exits the liquid lens 10 through the second window 32. In an embodiment, as explained, the first substrate 30 and the second substrate 36 are sufficiently transparent to allow the desired wavelength of electromagnetic radiation 47 to pass. The desired wavelength of electromagnetic radiation 47 exiting the second window 38 can be sensed by a sensor (not illustrated).

[0054] In some embodiments, one or both of the outer surface 68 of the first substrate 30 and the outer surface 70 of the second substrate 36 are substantially planar. Thus, because the liquid lens 10 can function as a lens (e.g., by refracting electromagnetic radiation 46 that passes through the interface 52), the outer surfaces 68, 70 of the liquid lens 10 can be flat, rather than curved like the outer surface of a fixed lens. In other embodiments, one or both of the outer surfaces 68, 70 are curved (e.g., concave or convex).

[0055] In an embodiment, the liquid lens 10 includes a power source connected to the first electrode 20 and the second electrode 24. In an embodiment, although not shown, the first electrode 20 is grounded via a first lead, and the second electrode 24 is connected to the power source via a second lead. In an embodiment, although not shown, the first electrode 20 is connected to the power source via a first lead, and the second electrode 24 is grounded via a second lead. As used herein, grounding refers to a connection to the earth or another large charge reservoir (e.g., a large conductor). As used herein, a power source is any device capable of establishing a potential difference. In an embodiment, the potential difference is in the range of about 0V to 120V, for example, 25V to 70V.

[0056] Applying a potential difference between the first electrode 20 and the second electrode 24 by a power source can change the shape of the lens formed by the interface 52 between the first liquid 48 and the second liquid 50. Without wishing to be bound by theory, by adjusting the potential difference applied between the first electrode 20 and the second electrode 24, the lens formed by the interface 52 between the first liquid 48 and the second liquid 50 can be adjusted using the electrowetting phenomenon. In an embodiment, adjusting the applied voltage changes the focal length of the lens. For example, such a focal length change enables the liquid lens 10 to perform an autofocus function. As used herein, the optical power of a lens is measured using diopters, which is the inverse of the focal length of the lens. In some embodiments, the optical power can be adjusted by about 0.25 diopters (D) or more, about 1D or more, about 2D or more, about 5D or more, about 40D or less, about 30D or less, about 20D or less, or about 10D or less. In some embodiments, the optical power of the lens can be adjustable in the following ranges: about -20D to about 20D, about -15D to about 15D, about -10D to about 10D, about -5D to about 5D, about -2D to about 2D, about 0D to about 20D, about 0D to about 10D, about 0D to about 5D, about 0D to about 2D, or any range or sub-range therebetween.

[0057] Additionally or alternatively, a potential difference is applied between the first electrode 20 and the second electrode 24 by a power source so that the interface 52 is tilted relative to the optical axis 22 of the liquid lens 10. This tilting enables the liquid lens 10 to perform an optical image stabilization ("OIS") function. Adjusting the interface 52 (e.g., tilting the interface 52, changing the shape of the interface 52) can be achieved without the liquid lens 10 physically moving relative to the image sensor, fixed lens or lens stack, housing, or other components of the camera module or other module in which the liquid lens 10 may be contained. In an embodiment, an alternating current electrical power is applied to the drive electrode 34 to manipulate the interface 52 between the first liquid 48 and the second liquid 50.

[0058] First Liquid 48

[0059] In an embodiment, the first liquid 48 is a non-conductive liquid. In an embodiment, the first liquid 48 is a non-polar liquid. As used herein, the term "non-conductive fluid" refers to a liquid having an electrical conductivity of less than about 1x10 -8 S / m, less than about 1x10 -10 S / m, or less than about 1x10 -14 S / m of liquid.

[0060] The first liquid 48 contains a polyfluoro aromatic compound represented by the following formula (I): (I) F x —(Aromatic)—Y—R1 wherein x is in the range of 2 to 5; wherein Y is any organic or inorganic moiety; and wherein R1 is any organic group. "Aromatic" herein means any six-carbon aromatic ring (e.g., benzene and derivatives). For Fx, where x is in the range of 2 to 5, it means that the degree of fluorination of the aromatic ring is 2 to 5 (e.g., there are 2 to 5 fluorine atoms bonded to the carbons of the six-carbon aromatic ring).

[0061] In an embodiment, Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S. In an embodiment, R1 is selected from a linear aliphatic chain, alicyclic, fluoroalicyclic and aromatic residues. "Alk" as used herein means any aliphatic chain and may be the same or different from that extending from Si or Ge. The composition of Y and R1 is not limited to those specifically mentioned. In an embodiment, Y and R1 are connected by a double bond or a triple bond.

[0062] In an embodiment, the first liquid 48 contains a polyfluoro aromatic compound represented by the following formula (II), which is an example of a polyfluoro aromatic compound of formula (I): wherein x is in the range of 2 to 5; wherein Y is any organic or inorganic moiety; and wherein R1 is any organic group. In an embodiment, Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S. In an embodiment, R1 is selected from a linear aliphatic chain, alicyclic, fluoroalicyclic and aromatic residues. The composition of Y and R1 is not limited to those specifically mentioned. In an embodiment, Y and R1 are connected by a double bond or a triple bond.

[0063] In an embodiment, the first liquid 48 contains a polyfluoro aromatic compound represented by the following formula (III), which is another example of a polyfluoro aromatic compound of formula (I): wherein x is in the range of 2 to 4; wherein Y is any organic or inorganic moiety; wherein R1 is any organic group; and wherein R2 is any organic group (and may be the same as or different from R1). In an embodiment, Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S. In an embodiment, R1 is selected from a linear aliphatic chain, alicyclic, fluoroalicyclic and aromatic residues. In an embodiment, R2 is an aliphatic group. The composition of Y, R1 and R2 is not limited to those specifically mentioned. In an embodiment, Y and R1 are connected by a double bond or a triple bond.

[0064] In an embodiment, the first liquid 48 includes butylpentafluorobenzene, which is represented by the following formula (IV): Butylpentafluorobenzene is an example with respect to formula (I) and (II) above, wherein Y is CH2.

[0065] In an embodiment, the first liquid 48 includes dimethyl nonafluorohexyl pentafluorophenyl silane, which is represented by the following formula (V): Dimethylnonafluorohexylpentafluorophenylsilane is an example for formula (I) and (II) above, where Y is Si(Alk)2.

[0066] In an embodiment, the first liquid 48 includes trimethylpentafluorophenylgermane, which is represented by the following formula (VI): Trimethylpentafluorophenylgermane is an example for formula (I) and (II) above, where Y is Ge(Alk)2.

[0067] In an embodiment, the first liquid 48 includes butoxypentafluorobenzene, which is represented by the following formula (VII): Butoxypentafluorobenzene is an example with respect to formulae (I) and (II) above, wherein Y is O (oxygen atom).

[0068] In an embodiment, the first liquid 48 includes cyclopentyloxypentafluorobenzene, which is represented by the following formula (VIII): Cyclopentyloxypentafluorobenzene is an example with respect to the above formulae (I) and (II) wherein Y is O (oxygen atom).

[0069] In an embodiment, the first liquid 48 includes 1-n-octyloxypentafluorobenzene, which is represented by the following formula (IX): 1-n-octyloxypentafluorobenzene is an example with respect to the above formulae (I) and (II) wherein Y is O (oxygen atom).

[0070] In an embodiment, the first liquid 48 includes cyclooctyloxypentafluorobenzene, which is represented by the following formula (X): Cyclooctyloxypentafluorobenzene is an example with respect to formulae (I) and (II) above, wherein Y is O (oxygen atom).

[0071] In an embodiment, the first liquid 48 includes 1-n-dodecyloxypentafluorobenzene, which is represented by the following formula (XI): 1-n-dodecyloxypentafluorobenzene is an example with respect to the above formulae (I) and (II) wherein Y is O (oxygen atom).

[0072] In an embodiment, the first liquid 48 includes cyclopentyl pentafluorophenyl sulfide, which is represented by the following formula (XII): Cyclopentyl pentafluorophenyl sulfide is an example with respect to the above formulae (I) and (II) wherein Y is S (sulfur atom).

[0073] In an embodiment, the first liquid 48 contains phenoxypentafluorobenzene, which is represented by the following formula (XIII): Phenoxypentafluorobenzene is an example with respect to formulae (I) and (II) above, wherein Y is O (oxygen atom).

[0074] In an embodiment, the first liquid 48 contains 2,4-difluoroanisole, which is represented by the following formula (XIV): 2,4-Difluoroanisole is an example with respect to the above formulae (I) and (II) wherein Y is O (oxygen atom).

[0075] In an embodiment, the first liquid 48 includes heptafluoropentyloxypentafluorobenzene, which is represented by the following formula (XV): Heptafluoropentyloxypentafluorobenzene is an example with respect to the above formulae (I) and (II) wherein Y is O (oxygen atom).

[0076] In an embodiment, the first liquid 48 comprises a mixture of more than one polyfluoro aromatic compound of the present disclosure, for example, more than one polyfluoro aromatic compound represented by formulas (IV)-(XV) above.

[0077] Table 1 below illustrates selected properties of the polyfluoroaromatic compounds of formula (IV)-(XV). In the above Table 1, "ρ" means density, "n" means refractive index, "ν" means kinematic viscosity, "V" means Abbe number, and "CTE" means coefficient of thermal expansion. Again, the polyfluoro aromatic compounds represented by formulas (IV)-(XV) are examples of compounds more broadly represented by formulas (I) and (II), and are not intended to limit the scope of polyfluoro aromatic compounds more broadly represented by formulas (I)-(III) and that can be included as a component of the first liquid 48.

[0078] Table 1 above demonstrates that exemplary polyfluoro aromatic compounds of the present disclosure can include a desired relatively low refractive index (e.g., in the range of 1.35 to 1.50) while also having a desired relatively high density (e.g., in the range of 1.1 g / mL to 1.5 g / mL) or molecular weight. Without being bound by theory, it is believed that the changes in these properties are the result of specifically tailoring the degree of fluorination of the six-carbon aromatic ring (the value of x in Fx) and specifically tailoring the Y segments and R groups on the polyfluoro aromatic ring. In some examples, adjusting the R groups allows the refractive index and viscosity of the first liquid 48 to be adjusted to the desired amount.

[0079] As mentioned above, the polyfluoro aromatic compounds described herein have exhibited several physical properties that are particularly beneficial for applications in making liquid lenses or electrowetting optical devices. First, the density of the polyfluoro aromatic compounds of the present disclosure is tunable. Providing a degree of fluorination of 2 or greater provides a mechanism for adjusting the density of the polyfluoro aromatic compound, and therefore provides a mechanism for adjusting the density of the first liquid 48 (of which the polyfluoro aromatic compound is a component). The density of the polyfluoro aromatic compounds of formula (I)-(III) increases with the F x In an embodiment, the density of the polyfluoro aromatic compound of the present disclosure is 1.1 g / mL, 1.2 g / mL, 1.3 g / mL, 1.4 g / mL, 1.5 g / mL, or within any range bounded by any two of these values ​​(e.g., 1.1 g / mL to 1.5 g / mL, 1.2 g / mL to 1.4 g / mL, etc.). In an embodiment, the density of the polyfluoro aromatic compound of the present disclosure is greater than 1.1 g / mL, greater than 1.2 g / mL, greater than 1.3 g / mL, or greater than 1.4 g / mL. All density values ​​described herein are density values ​​at 20°C.

[0080] Second, the hydrophobicity of the polyfluoro aromatic compounds of the present disclosure is adjustable. Therefore, the degree of immiscibility of the first liquid 48 (of which the polyfluoro aromatic compound is a component) in the second liquid 50 is adjustable. As mentioned above, the first liquid 48 and the second liquid 50 should be immiscible. As the degree of fluorination of the polyfluoro aromatic compounds of the present disclosure increases, the hydrophobicity of the polyfluoro aromatic compounds increases, and therefore, the miscibility of the first liquid 48 with the second liquid 50 decreases. In an embodiment, the solubility of the first liquid 48 in water at 22-25°C is less than about 2g / 100ml, for example about 0.5g / 100ml at 22-25°C.

[0081] Third, the polyfluoro aromatic compounds of the present disclosure are highly miscible with many different classes of hydrophobic compounds. Formulating the first liquid 48 to have the above-mentioned properties and, in particular, to have a beneficial boiling point, surface energy, coefficient of thermal expansion (CTE), and density matching with the second liquid 50 may be difficult. Therefore, the first liquid 48 may be a mixture of one or more other substances in addition to the polyfluoro aromatic compounds of the present disclosure. As described herein, the polyfluoro aromatic compounds of the present disclosure are highly miscible with many different classes of hydrophobic compounds, which together may form the first liquid 48. .

[0082] In this regard, in an embodiment, in addition to one or more polyfluoro aromatic compounds of the present disclosure, the first liquid 48 further comprises one or more inorganic liquids (e.g., silicone oil), one or more alkanes (e.g., hexane, heptane, octane, nonane, decane, dodecane), one or more aromatic compounds (e.g., benzene, toluene, diphenyldimethylsilane, 2-(ethylthio)benzothiazole, 1-chloronaphthalene, benzothiophene, 4-bromodiphenyl ether, 1-phenylnaphthalene, 2,5-dibromotoluene, phenyl sulfide), one or more other fluorinated hydrocarbons that do not satisfy the above formulas (I)-(III), one or more fluorinated silicones, one or more organic germanium compounds (e.g., tetramethylgermane, tetraethylgermane, hexamethyldigermane, hexaethyldigermane, diphenyldimethylgermane, phenyltrimethylgermane), or combinations thereof. It should be understood that the first liquid 48 may be entirely composed of one or more polyfluoro aromatic compounds of the present disclosure.

[0083] Further, the polyfluoroaromatic compounds of the present disclosure are relatively inexpensive to formulate, have a desirable refractive index, and have high hydrolytic stability.

[0084] In an embodiment, the viscosity of the first liquid 48 is in the range of about 0.5 centistokes (cSt) to 5.0 centistokes (at 20° C.), for example 0.5 cSt to 5.0 cSt (at 20° C.) In an embodiment, the refractive index of the first liquid 48 is in the range of 1.38 to 1.75 (589 nm, 20° C.).

[0085] In an embodiment, the density of the first liquid 46 is 0.95 g / mL, 1.00 g / mL, 1.05 g / mL, 1.10 g / mL, 1.15 g / mL, 1.20 g / mL, 1.25 g / mL, 1.30 g / mL, or 1.35 g / mL, or within any range bounded by any two of these values ​​(e.g., 0.95 g / mL to 1.35 g / mL, 1.10 g / mL to 1.30 g / mL, etc.).

[0086] The optical quality of a liquid lens can be specified by the wavefront error (WFE). The WFE characterizes the deviation of the actual shape of the liquid lens 10 from a perfect spherical mirror and is measured in nanometers as root mean square (RMS).

[0087] An important physical parameter of the liquid lens 10 is the "contact angle" value. When the liquid lens 10 moves the interface 52 between the first liquid 48 and the second liquid 50, the angle between the first liquid 48 (non-conductive) surrounded by the second liquid 50 (conductive) and the insulating layer 54 can be characterized and called the "contact angle". The "contact angle" is voltage dependent.

[0088] In addition to WFE, the optical quality of the liquid lens 10 can be defined by contact angle hysteresis (e.g., at the interface 52). The contact angle hysteresis can be defined as the difference in measured contact angles of the first liquid 48 and the insulating layer 54 at a given voltage when the potential difference between the first electrode 20 and the second electrode 24 is increased and then reduced (e.g., the voltage is ramped up from 0V to a maximum drive voltage and then the voltage is ramped down back to 0V). In other words, the contact angle hysteresis can be defined by the difference between the contact angle observed for a given voltage value during the voltage ramp up and the value observed for the same voltage during the voltage ramp down. In some examples, the initial contact angle without applied voltage can include a maximum value of about 25° and can increase to about 100° or more at the "maximum drive voltage" due to the electrowetting effect. In some examples, the maximum drive voltage can provide an AC 1kHz voltage. The first liquid 48 and the second liquid 50 can have an optical refractive index difference. Therefore, by comparing the optical power (e.g., in diopters) or focal length (e.g., in meters) of liquid lens 10 at increasing voltage to the optical power or focal length of liquid lens 20 at the same decreasing voltage, contact angle hysteresis can be measured as optical hysteresis.

[0089] During operation of the liquid lens 10, the properties of the liquid lens 10 and its components may change, which affects the reliability of the liquid lens 10. For example, the dielectric properties of the first liquid 48, the second liquid 50, and / or the insulating layer 54 may change in response to exposure to voltage differences, temperature changes, and other factors over time. Further, the surface energy of the insulating layer 54 may change in response to exposure to the first liquid 48 and the second liquid 50 over time. Deviations in these properties of the liquid lens 10 may reduce the reliability and performance characteristics of the liquid lens 10 (e.g., the optical quality or stability of the liquid lens 10 may be affected).

[0090] Reliability can be one of the most difficult aspects to achieve in liquid lens design. Most reliability tests are based on exposing a liquid lens (e.g., liquid lens 10) to high or low temperatures, voltage, acceleration, electromagnetic radiation, or a combination thereof. Typically, a liquid lens (e.g., liquid lens 10) is measured before and after exposure to a reliability test, and key parameters (WFE, hysteresis, etc.) are compared. Significant increases in WFE and hysteresis are undesirable.

[0091] Since the second liquid 50 generally contains water, glycol or ionic liquid, the second liquid 50 may contain a significant concentration of nucleophilic substances. Therefore, the compounds present in the first liquid 48 should not be structures that are sensitive to nucleophilic substances. For example, structures with low hydrolytic stability are undesirable. During reliability testing, chemical evolution of the first liquid 48 may lead to an increase in hysteresis.

[0092] In this regard, the first liquid 48 comprising the polyfluoro aromatic compound of the present disclosure imparts beneficial properties to the liquid lens 10. Since the CF bond in the composition of formula (I) is significantly stronger than C-Cl or C-Br, the fluoroaromatic structure comprising at least two fluorine substituents as described herein should have improved hydrolytic stability when compared to other halogenated structures that do not comprise at least two fluorine substituents. Further, the Y moiety in the above formulas (I)-(III) can be selected to impart high hydrolytic stability (e.g., highly resistant to hydrolysis). In an embodiment, after storage at 85° C. for at least 120 hours, the liquid lens 10 comprising the first liquid 48 as described herein exhibits a hysteresis that increases by less than 1 diopter relative to the initial hysteresis.

[0093] As further disclosed in the Examples below, the polyfluoroaromatic compounds of the present disclosure are relatively inexpensive to produce. Raw materials from which fluoroaromatic compounds (eg, polyfluorobenzenes) can be produced are readily available.

[0094] Further, as mentioned, the first liquid 48 described herein comprising one or more fluoroaromatic compounds of the present disclosure can be compatible with the substantially water-free second liquid 50. This is advantageous because many non-conductive liquids used in liquid lenses are not compatible with substantially water-free conductive liquids.

[0095] Reference now Figure 2 , a method 100 of making a liquid lens 10 is described herein. At step 102, the method 100 includes disposing a first liquid 48 in a substrate 12. At step 104, the method also includes disposing a second liquid 50 in the substrate. In embodiments, step 104 occurs before step 102. In other embodiments, step 104 occurs after step 102. As mentioned, the first liquid 48 and the second liquid 50 are substantially immiscible, and an interface 52 is formed between the first liquid and the second liquid 50.

[0096] The following examples describe various features and advantages provided by the present disclosure and are in no way intended to limit the present invention and the appended claims. It should be understood that the first liquid 48 can be synthesized according to other processes. It should also be understood that the following examples may include additional or alternative steps without departing from the scope of the present disclosure. Example

[0097] Example 1 - In Example 1, a liquid lens was formed. The conductive liquid was electrolyte-based and contained about 93 wt% ethylene glycol, about 3 wt% water, and about 4 wt% potassium acetate. The non-conductive liquid was oil-based and contained about 35 wt% phenyltrimethylsilane and about 65 wt% phenoxypentafluorobenzene.

[0098] Example 2 - In Example 2, another liquid lens was formed. The conductive liquid was electrolyte-based, comprising about 93 wt% ethylene glycol, about 3 wt% water, and about 4 wt% potassium acetate. The non-conductive liquid was oil-based, comprising about 15 wt% diphenyldimethylsilane, about 25 wt% n-octyltris(trimethylsiloxy)silane, and about 60 wt% cyclopentylpentafluorophenyl sulfide.

[0099] Example 3 - In Example 3, a liquid lens was formed. The conductive liquid was electrolyte based, comprising about 90 wt% 1-ethyl-3-methylimidazolium dicyanamide and about 10 wt% propylene carbonate. The non-conductive liquid was oil based, comprising about 10 wt% n-octyl(trimethylsiloxy)silane and about 90 wt% 1-n-octyloxypentafluorobenzene.

[0100] Example 4 - In Example 4, a non-conductive liquid suitable for a liquid lens containing butyl pentafluorobenzene is formed. As an initial step, 85 mL of 2.5 M n-butyl lithium is diluted in hexane and 70 mL of dry tetrahydrofuran (THF). This solution is then slowly added to a solution of 40.2 g (0.21 mol) of hexafluorobenzene in 230 mL of dry THF and cooled in a dry ice / acetone bath. At the end of the addition, the temperature is maintained at -78°C for 20 minutes. Next, the reaction is quenched by adding 10 mL of water, followed by 120 mL of brine. Then, 150 mL of ether is added and the phases are separated. The remaining product is extracted from the aqueous phase with ether (3x50 mL). The ether phases are then recombined, dried over magnesium sulfate and concentrated under reduced pressure. The crude product is evaporated to give two fractions: butyl pentafluorobenzene, 28.16 g (12 mmol) (yield 60%) and o-dibutyl pentafluorobenzene, 5.94 g (2.2 mmol).

[0101] As illustrated in this example, butylpentafluorobenzene can be formed by nucleophilic substitution with an organometallic reactant on a polyfluorobenzene (e.g., hexafluorobenzene) or by photocatalyzed CF alkylation. Optionally, nucleophilic substitution can be performed with a Grignard reagent and hexafluorobenzene and provide the same or similar results.

[0102] Example 5 - In Example 5, a non-conductive liquid suitable for a liquid lens comprising dimethyl nonafluorohexyl pentafluorophenyl silane is formed. As an initial step, 2 mL (3.9 g, 15.8 mmol) of bromopentafluorobenzene is diluted in 200 mL of dry ethanol and the solution is placed in an ice bath. Then, 6 mL of 2.5 M n-butyl lithium (in hexane) is slowly added to the bromopentafluorobenzene solution over a duration of 15 minutes. Then 3.7 mL (14.8 mmol) of dimethyl nonafluorohexyl chlorosilane is added. The mixture is stirred at room temperature for 1 hour and 30 minutes. Then, the reaction is quenched by adding 30 mL of water. Then, 50 mL of ether is added to the solution and the phases are separated. The remaining product is extracted from the aqueous phase with ether (2x40 mL). The ether phases are then recombined, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel using pentane to give the desired product as an uncolored, or colorless oil, including 7.7 g of dimethylnonafluorohexylpentafluorophenylsilane in quantitative yield.

[0103] Optionally, the same procedure can be used with any chlorosilane or chlorogermane to give the coupled adduct.

[0104] Example 6 - In Example 6, a non-conductive liquid suitable for a liquid lens is formed containing 1-n-dodecyloxypentafluorobenzene. As an initial step, 2.5 mL (27.2 mmol) of a suspension of potassium hydride in mineral oil is placed in a round-bottom flask under an inert atmosphere. Next, the suspension is washed three times with 10 mL of pentane to remove the initial mineral oil and dispersed in 25 mL of dry THF. Then, 3.9 mL (33.5 mmol) of hexafluorobenzene is added and the mixture is placed in an ice bath. Next, 5 mL (22.3 mmol) of dodecanol is added dropwise. After the addition is complete, the mixture is kept in an ice bath for 30 minutes and then placed at room temperature. After 1 hour and 30 minutes, the reaction is quenched by adding 30 mL of water. Then, 60 mL of water is added and the phases are separated. The remaining product is extracted from the aqueous phase with ether (2x60 mL). The ether phases are then recombined, dried over magnesium sulfate and concentrated under reduced pressure. The crude product was purified by flash chromatography on silica gel using pentane to give 4.57 g (yield 58%) of the desired product, 1-n-dodecyloxypentafluorobenzene, as a colorless oil.

[0105] This example illustrates the nucleophilic substitution of the fluoride anion on a polyfluorobenzene by an alkoxide and the formation of a carbon-oxygen bond from hexafluorobenzene to synthesize 1-n-dodecyloxypentafluorobenzene.

[0106] Example 7 - In Example 7, a non-conductive liquid suitable for a liquid lens was formed containing cyclopentyl pentafluorophenyl sulfide. As an initial step, 10 mL of cyclohexane, 1.2 mL (8.95 mmol) of pentafluorobenzenethiol and 0.68 mL (7.45 mmol) of cyclopentene were added to a culture tube and stirred under argon. Next, 10 mg (0.0373 mmol) of a photocatalyst represented by the following formula (XVI) was added. The culture tube was then sealed and placed in a closed box equipped with a blue LED and a cold water bath (5 ° C). Irradiation mixture and stirring at room temperature for 48 hours. Then water and ether were added. Then, each layer was separated and the organic phase was washed with a saturated solution of NaHCO (2x20 mL). The ether phase was collected, dried over magnesium sulfate, filtered and concentrated in vacuo to obtain a yellow liquid. Then pentane was used, the crude product was purified on spherical silica gel to obtain the cyclopentyl pentafluorophenyl sulfide desired product of 1.49g (yield 74%), which was a colorless liquid.

[0107] This example illustrates the photocatalytic addition of fluorothiophenols (pentafluorothiobenzene) to olefins to synthesize cyclopentyl pentafluorophenyl sulfide. It will be apparent to those skilled in the art that various modifications and variations can be made without departing from the spirit or scope of the claims.

Claims

1. A liquid lens, comprising: A first liquid comprising a polyfluoro aromatic compound represented by formula (I) (I)F x —(Aromatic)—Y—R1 wherein x is in the range of 2 to 5; wherein Y is any organic or inorganic moiety; wherein R1 is any organic group; and "aromatic" is any six-carbon aromatic ring; Wherein, after storage at 85° C. for at least 120 hours, the liquid lens exhibits a hysteresis that increases by less than or equal to 1 diopter relative to the initial hysteresis.

2. The liquid lens according to claim 1, wherein: Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "Alk" is a linear aliphatic chain.

3. The liquid lens according to claim 1, wherein: R1 is selected from linear aliphatic chains, alicyclic, fluoroalicyclic and aromatic residues.

4. The liquid lens according to claim 1, wherein: F of formula (I) x The (aromatic) part is a fluorinated benzene ring.

5. The liquid lens according to claim 1, wherein: F of formula (I) x The (aromatic) moiety is a pentafluorobenzene ring containing five fluorine substituents.

6. The liquid lens according to claim 1, wherein: The polyfluoro aromatic compound is represented by the following formula (II): wherein x is in the range of 2 to 5; wherein Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "alk" is a linear aliphatic chain; and wherein R1 is selected from a linear aliphatic chain, alicyclic, fluoroalicyclic and aromatic residues.

7. The liquid lens according to claim 1, wherein: The polyfluoro aromatic compound is represented by the following formula (III): wherein x is in the range of 2 to 4; wherein Y is any organic or inorganic moiety; wherein R1 is any organic group; and wherein R2 is any organic group.

8. The liquid lens according to claim 1, further comprising: The second liquid, wherein the first liquid and the second liquid (i) form an interface between the first liquid and the second liquid, and (ii) comprise less than 2% miscibility within a temperature range of -30°C to 85°C; and The first liquid comprises a density (at 20° C.) of 0.95 g / mL to 1.35 g / mL.

9. The liquid lens according to claim 8, wherein: The second liquid is substantially free of water.

10. A liquid lens, comprising: The first liquid comprises a polyfluoro aromatic compound represented by the following formula (I): (I)F x —(Aromatic)—Y—R1 wherein x is in the range of 2 to 5; wherein Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "Alk" is a linear aliphatic chain; wherein R1 is any organic group, and "aromatic" is any six-carbon aromatic ring; and The second liquid, wherein the first liquid and the second liquid (i) form an interface between the first liquid and the second liquid, (ii) comprise less than 2% miscibility within a temperature range of -30°C to 85°C; and (iii) each comprise a density that differs by less than 0.1 g / mL.

11. The liquid lens according to claim 10, wherein: R1 is selected from linear aliphatic chains, alicyclic, fluoroalicyclic and aromatic residues.

12. The liquid lens according to claim 10, wherein: F of formula (I) x The (aromatic) part is a fluorinated benzene ring.

13. The liquid lens according to claim 10, wherein: F of formula (I) x The (aromatic) moiety is a pentafluorobenzene ring containing five fluorine substituents.

14. The liquid lens according to claim 10, wherein: The polyfluoro aromatic compound is represented by the following formula (II): wherein x is in the range of 2 to 5; wherein Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "alk" is a linear aliphatic chain; and wherein R1 is selected from a linear aliphatic chain, alicyclic, fluoroalicyclic and aromatic residues.

15. The liquid lens according to claim 10, wherein: The polyfluorinated aromatic compound is selected from the group consisting of: Butylpentafluorobenzene; Dimethylnonafluorohexylpentafluorophenylsilane; Trimethylpentafluorophenylgermane; Butoxypentafluorobenzene; Cyclopentyloxypentafluorobenzene; 1-n-octyloxypentafluorobenzene; Cyclooctyloxypentafluorobenzene; 1-n-Dodecyloxypentafluorobenzene; Cyclopentyl pentafluorophenyl sulfide; Phenoxypentafluorobenzene; 2,4-Difluoroanisole; and Heptafluoropentyloxypentafluorobenzene.

16. The liquid lens according to claim 10, wherein: The polyfluoro aromatic compound is represented by the following formula (III): wherein x is in the range of 2 to 4; wherein Y is any organic or inorganic moiety; wherein R1 is any organic group; and wherein R2 is any organic group.

17. The liquid lens according to claim 10, wherein The first liquid comprises a density (at 20° C.) of 0.95 g / mL to 1.35 g / mL; and The second liquid is water-based, glycol-based, or ionic liquid-based.

18. The liquid lens according to claim 10, wherein: The second liquid is substantially free of water.

19. A method for manufacturing a liquid lens, the method comprising: A first liquid is provided in the substrate, wherein the first liquid comprises a polyfluoro aromatic compound represented by the following formula (I): (I)F x —(Aromatic)—Y—R1 wherein x is in the range of 2 to 5; wherein Y is selected from CH2, Si(Alk)2, Ge(Alk)2, O and S, wherein "Alk" is a linear aliphatic chain; wherein R1 is any organic group, and "aromatic" is any six carbon aromatic ring; and disposing a second liquid in the substrate, wherein the first liquid and the second liquid (i) form an interface between the first liquid and the second liquid, and (ii) comprise less than 2% miscibility within a temperature range of -30°C to 85°C; wherein the first liquid comprises a density (at 20° C.) of 0.95 g / mL to 1.35 g / mL; wherein the difference between the density of the first liquid and the density of the second liquid is less than 0.1 g / mL; and Wherein, the difference between the refractive index of the first liquid and the refractive index of the second liquid is in the range of 0.02 to 0.

24.

20. The method of claim 19, wherein: F of formula (I) x - the (aromatic) moiety is a fluorinated benzene ring; and The second liquid is substantially free of water.

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