A fluorine-containing ether compound according to the present invention is a fluorine-containing ether compound represented by the following General Formula (1). ##STR00001##

This fluorine-containing ether compound is represented by Formula (1).

R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5  (1) (in Formula (1), R.sup.1 is an aryl group or an aralkyl group, R.sup.2 is a divalent linking group having 0 or 1 polar group, R.sup.3 is a perfluoropolyether chain, R.sup.4 is a divalent linking group having 2 or 3 polar groups, and R.sup.5 is an aryl group or an aralkyl group.)

This fluorine-containing ether compound is represented by formula (1) shown below.

R.sup.1—CH.sub.2—R.sup.2—CH.sub.2—R.sup.3  (1)

In formula (1), R.sup.2 is a perfluoropolyether chain represented by a formula (2) shown below. R.sup.1 is a terminal group that is bonded to R.sup.2 via a CH.sub.2 group, and is represented by a formula (3) shown below. R.sup.3 is bonded to R.sup.2 via a CH.sub.2 group, is a terminal group having at least one hydroxyl group, and may be the same as, or different from, R.sup.1.

—(CF.sub.2).sub.p-1—O—((CF.sub.2).sub.pO).sub.q—(CF.sub.2).sub.p-1—  (2)

In formula (2), p represents an integer of 2 to 3, and q indicates the average polymerization degree and is a number within a range from 1 to 20.

—O(CH.sub.2—CH(OH)—CH.sub.2—O).sub.2—CH.sub.2—(CH.sub.2).sub.n,—OH  (3)

In formula (3), n represents an integer of 1 to 8.

There is provided a fluorine-containing ether compound represented by the following formula. R.sup.1—R.sup.2—CH.sub.2—R.sup.3—CH.sub.2—OCH.sub.2CH(OH)CH.sub.2O—CH.sub.2—R.sup.3—CH.sub.2—R.sup.4—R.sup.5 (in the formula, R.sup.3 represents a perfluoropolyether chain; R.sup.2 and R.sup.4 represent a divalent linking group having a polar group and may be the same or different from each other; R.sup.1 and R.sup.5 represent a terminal group bonded to an oxygen atom of R.sup.2 or R.sup.4 and may be the same or different from each other; and at least one of R.sup.1 and R.sup.5 is an organic group having 1 to 8 carbon atoms and at least one of hydrogens included in the organic group is substituted by a cyano group).

A fluorine-containing ether compound according to the present invention is expressed by the following formula (1) or the following formula (2):

Q.sup.1{—(R.sup.f12).sub.m2—O—(R.sup.f11O).sub.m1-A.sup.1}.sub.n1  Formula (1)

{A.sup.1-(OR.sup.f11).sub.m1—O—(R.sup.f12).sub.m2-}.sub.n2Q.sup.2-[(R.sup.f12).sub.m2—O—(R.sup.f11O).sub.m1—(R.sup.f12).sub.m2-Q.sup.3].sub.p—(R.sup.f12).sub.m2—O—(R.sup.f11O).sub.m1—(R.sup.f12).sub.m2-Q.sup.2-{(R.sup.f12).sub.m2—O—(R.sup.f11O).sub.m1-A.sup.1}.sub.n2  Formula (2),

wherein Q.sup.1, Q.sup.2, Q.sup.3, R.sup.f11, R.sup.f12, A.sup.1, n1, n2, m1, m2, and p are as described in the specification.

A polar compound has a high chemical stability, high ability to align liquid crystal molecules and high solubility in a liquid crystal composition, and causes no decrease of liquid crystallinity of the liquid crystal composition, a liquid crystal composition contains the compound, and a liquid crystal display device includes the composition. The compound is represented by formula (1), the composition contains the compound, and the liquid crystal display device uses the composition. ##STR00001## In formula (1), R.sup.1 is alkyl having 3 to 15 carbons, alkenyl having 4 to 15 carbons or the like; a is an integer from 2 to 12; and R.sup.2 is a group represented by formula (1a), formula (1b) or formula (1c). ##STR00002## In the formulas, S.sup.1 and S.sup.2 are independently a single bond, alkylene having 1 to 10 carbons; S.sup.3 is >CH— or >N—; S.sup.4 is >C< or >Si<; and X.sup.1 is —OH, —NH.sub.2 or the like.

A method of making a functionalized fluorinated monomer for use in making oligomers and polymers that can be used to improve surface properties of polymer-derived systems, such as coatings. The method of making a functionalized fluorinated monomer includes reacting at least one fluorinated nucleophilic reactant, such as a fluorinated alcohol, with at least one compound containing at least one epoxide group. Other methods include reaction of a fluorinated alcohol with a cyclic carboxylic anhydride. In another embodiment, a method includes reacting a fluorinated mesylate, tosylate or triflate with an amine, alkoxide or phenoxide. In other embodiments, the method includes reacting a fluorinated alcohol with an alkyl halide, or reacting a fluorinated alkyl halide with an amine. The functionalized fluorinated monomers may be used as intermediates and reacted to modify the functional groups thereon. Further, the functionalized fluorinated monomers may be reacted to form polymers or oligomers, or with polymers or oligomers having functional groups to modify the polymer or oligomer through the functional group thereon.

A method of making a functionalized fluorinated monomer for use in making oligomers and polymers that can be used to improve surface properties of polymer-derived systems, such as coatings. The method of making a functionalized fluorinated monomer includes reacting at least one fluorinated nucleophilic reactant, such as a fluorinated alcohol, with at least one compound containing at least one epoxide group. Other methods include reaction of a fluorinated alcohol with a cyclic carboxylic anhydride. In another embodiment, a method includes reacting a fluorinated mesylate, tosylate or triflate with an amine, alkoxide or phenoxide. In other embodiments, the method includes reacting a fluorinated alcohol with an alkyl halide, or reacting a fluorinated alkyl halide with an amine. The functionalized fluorinated monomers may be used as intermediates and reacted to modify the functional groups thereon. Further, the functionalized fluorinated monomers may be reacted to form polymers or oligomers, or with polymers or oligomers having functional groups to modify the polymer or oligomer through the functional group thereon.

Provided herein is a lubricant including a compound of Formula I
L-(CF.sub.2CF.sub.2O).sub.n—CF.sub.2CH.sub.2O—N—OCH.sub.2CF.sub.2O—(CF.sub.2CF.sub.2O).sub.m-M  (Formula I)
wherein L is selected from the group consisting of ##STR00001## M is selected from the group consisting of ##STR00002##
wherein each instance of R.sup.1, R.sup.2, and R.sup.3 is independently selected from the group consisting of hydroxyl, alkoxyl, carbocycyl, phenyl, heterocycyl, piperonyl, carboxyl, alkylamido, acetamido, carbamoyl, N-alkylcarbamoyl, N,N-dialkylcarbamoyl, 2,3-dihydroxy-1-propoxyl, acryloyl, alkacryloyl, methacryloyl, a substituent of methyl methacrylate, and a substituent of glycidyl ether; and
wherein n≧1, m≧1, and n and m are the same or different.

The present invention relates to novel compounds containing fluorinated end groups, to the use thereof as surface-active substances, and to compositions comprising these compounds.