ZA200405773B - Bridged carbocyclic compounds and methods of making and using same. - Google Patents

Description

£°+2004/5773

A

CROSS REFERENCE TO RELATED APPLICATIONS

[0001] This application claims the benefit of U.S. Provisional Application No. 60/492,573, filed 08/04/2003.

BACKGROUND OF THE INVENTION

[0002] The present invention relates generally to bridged carbocyclic compounds. This invention also relates to the use of these compounds, for example, as monomers that can be homopolymerized or copolymerized with other reactive components to make resins within sub-200 nanometer (nm) photoresist compositions.

[0003] Photoresists are photosensitive films that are used for the transfer of images to a substrate. In a typical lithography process, a substrate is generally coated with either a positive or negative photoresist coating. The photoresist-coated substrate is then exposed through a photomask to an activating radiation source which transfers the pattern of the photomask onto the photoresist-coated substrate. Depending upon whether the photoresist coating is positive or negative, the radiation source either increases or decreases its solubility in a subsequently applied developer solution. Ina positive photoresist coating, the areas masked from the radiation source remain after development while the exposed areas are dissolved away whereas in a negative photoresist coating the opposite occurs. The patterned photoresist image acts as a

© e2004/5773 \ : mask for subsequent substrate patterning processes such as etching, doping, and/or coating with metals, other semiconductor materials, or insulating materials.

[0004] Current interest in the semiconductor industry has increased in photoresists that can be photoimaged with short wavelength radiation, i.e., exposure radiation of about 200 nm or less such as 193 nm (ArF laser) or 157 nm (F, excimer beam laser) wavelengths. Short exposure wavelengths may allow for the formation of smaller features within the semiconductor device. In this connection, a photoresist that can provide well-resolved images after exposure to a 193 nm or 157 nm wavelength radiation source may allow for the formation of relatively smaller (e.g., sub-0.25 pm) features.

Smaller device features meet the industry demands for smaller dimension circuit patterns and provide for greater circuit density and enhanced device performance.

[0005] Photoresist materials, particularly sub-200 nm materials, are particularly challenging to develop because of the need to balance a variety of different performance characteristics. Photoresist materials should ideally provide high transparency at the exposure wavelength, sufficient resistance to plasma-etching processes, and functional groups that are capable of undergoing sufficient photochemical transformations that change the solubility in developer solutions. Besides these, other important characteristics include, but are not limited to, reasonably simple synthesis procedures, adhesion to the underlying substrate, glass transition temperatures compatible with typical processing temperatures, acceptable shelf storage lifetime, and minimum toxicological risk.

[0006] The prior art discloses a variety of monomers that can be polymerized and used as base resins within photoresist compositions for sub-200 nm applications. For the higher end of this range (e.g. 193 nm), cycloaliphatic structures have drawn the most attention. For lower wavelength applications (e.g. 157 nm), the monomers tend to have one or more electron-withdrawing groups such as fluorine or hydroxy! and one or more

« £ «2004/5773 cyclic structures. Itis believed that the combination of the electron-withdrawing groups and the one or more cyclic structures improve the performance of the photoresist composition, particularly transparency.

[0007] The preparation of bicyclo[2.2.1]hept-5-ene-2-(1,1,1-trifluoro-2- trifluoromethylpropan-2-ol), also known as NBHFA, and its use in photoresist polymers was first described by H. Ito, et al., “Synthesis and Evaluation of Alicyclic Backbone

Polymers for 193 nm Lithography”, American Chemical Society, 1998. Since then it has become an industry benchmark for 157 nm photoresists. The norbornene monomers disclosed therein were synthesized by a Diels-Alder Reaction. One reaction disclosed within the reference is as follows:

FsC ee,

CF;

J . 170 °C ad 1) CFs

The optical density (OD) of the homopolymer (expressed as Absorption at 157 nm divided by the film thickness) was later reported to be 1.7 micrometers™ (Ito et al, SPIE

Proceedings, Vol. 4690 (2002), 18-28).

[0008] U.S. Patent Application US2002/0004570 (*Zampini |") describes photoresist compositions that contain polymerized units of cyclic olefin monomers having one or more pendant cyclic electron-withdrawing groups. The pendant cyclic electron- withdrawing groups disclosed may be N-based, O-based, or S-based,

[0009] European published patent application WO 02/21214 (“Zampini II") discloses base resins within 157 nm photoresist compositions that contain at least one electronegative group that includes aromatic groups such as phenolic moieties. In this x connection, Zampini Il specifically describes vinyl ether entities that incorporate fluorinated aromatic structures as the electronegative group.

[0010] European published patent application WO 02/21213 (“Taylor”) describes resins that are used within photoresist compositions that contain photoacid-labile deblocking groups substituted with one or more electron-withdrawing groups. The electron- withdrawing moieties within the resin are bonded to the blocking group so that the acid- catalyzed blocking and deblocking reactions are relatively unaffected by their presence.

[0011] Japanese Application JP 2002/179,731 (Chemical Abstracts 137:54625: "Harada I") discloses photoresist resins that contain the structure: CO,CR'R®R where

R'and R*=H, F, or a C15 alkyl and R=Cj. cyclic alkyl. In addition, Harada | describes an acrylate resin that contains fluorinated alkyl groups in ester side chains.

[0012] U.S. Patent Application 2002/0051936 (“Harada II") describes an acrylic resin that contains repeating units containing a fluorinated hydrocarbon group, an acid labile group, and an adhesive group. Harada Il describes one of the units, preferably the acid labile group, as having at least one alicyclic structure. Harada I} also describes acryiic polymers containing the structure ~O-C(R'R?%)-C(H)(R*R*, where R’, R, R®, and R* are

H, F, or an unsubstituted or fluorinated, straight, branched or cyclic alkyl group.

Transparencies are reported from 25 — 45 % for 200 nm films measured by transmission spectroscopy.

[0013] European Application EP 1 126 322 describes resins for use in a 157 nm photoresist that contain fluorinated ester groups. Transparencies are reported from 40 - 80 % for 300 nm films measured by transmission spectroscopy.

[0014] European Application EP 1,103,856 (“Tsutsumi”) describes a fluorine-containing resin that contains polymerized units of an acrylic or methacrylic acid ester wherein the ester moiety comprises a fluorine-containing group. Tsutsumi further describes moieties where the fluorine-containing group has a cyclic structure such as a fluorine-containing

. | "e200L/RTT3 benzene ring, a fluorine-containing cyclopentane ring, a fluorine-containing cyclohexane ring, or a fluorine-containing cycloheptane ring. Transparencies are reported from 51 — 68 % for 100 nm films measured by transmission spectroscopy.

[0015] US 0059710A1 discloses the following composition useful as a photoresist composition: 7 «

WG-0

R?

[0016] wherein Ris a hydrogen atom or an organic group; W2 is a linkage group; R'is a hydrogen atom or a hydroxyl-protecting group; and R? is a group containing a fluorine atom, where carbon atoms constituting the ring in the formula may each have a substituent. Additionally, US 0059710A1 discloses in Example 14, the reaction of 5- hydroxybicyclo[2.2.1]-2-heptene and hexafluoroacetone to produce 5-[1,1- bis(trifluoromethyl)-1-hydroxymethylJoxybicyclo[2.2.1]-2-heptene: = 0—C—OH &F,

[0017] WO 00/67072 discloses the following composition useful as a photoresist [Jor crecraon material:

[0018] As described in Example 3 of WO 00/67072, the photoresist material was made by reacting sodium hydride, hexafluoroisobutylene epoxide, and 5-norbornene-2- methanol in anhydrous DMF. Sodium hydride is pyrophoric, making this process difficult to commercialize.

%

[0019] Many of the monomers that are known to be useful in a photoresist material must be copolymerized with fluoroolefins or the like to form a useful photoresist material, for example, see the “Binder 2 Preparation Procedure” on page 24 of WO 02/31595 A2 which uses 70 parts TFE in a pressurized vessel when making a copolymer to be used 5S as a photoresist material. The tetrafluoroethylene provides improved transparency to the copolymer; however, the tetrafluoroethylene decreases the etch resistance, and causes poor adhesion, and additionally complicates the reaction to make the photoresist material.

[0020] Accordingly, there is a need in the art to provide novel resins polymerized from novel monomers that provide high transparency at sub-200nm wavelengths. These monomers can be used to make homopolymers useful as photoresist materials, if desired. There is also a need in the art for new industrial processes to make fluorine- containing monomers providing improved transparencies.

[0021] All references cited herein are incorporated herein by reference in their entirety.

BRIEF SUMMARY OF THE INVENTION

[0022] This invention provides a bridged carbocyclic compound comprising a bridged carbocyclic ring, and an alkoxide group, wherein an oxygen of the alkoxide group is bonded to a ring-member of said bridged carbocyclic ring and to a carbon of the alkoxide group, and further wherein the carbon of the alkoxide group bonded to said oxygen has at least one fluorine-containing group bonded to said carbon and further wherein the alkoxide group has at least one hydroxyl group separated from said carbon that is bonded to said oxygen and said fluorine-containing group by at least one additional carbon that is bonded to said carbon that is bonded to said oxygen.

[0023] This invention further provides a bridged carbocyclic compound having the following structure:

% _O0_ _A_ _OR!

Re Te

RER*R*R 0 where A is a single bond, or a divalent organic group having 1 to 20 carbon atoms, and B is a bridged carbocyclic group of the type:

R® 7

R10 rR!" RW (i) wherein Z is CH,, CHR", CR™R", CH,CH,, CH,CHR'S or a heteroatom; R'is a hydrogen, fluorinated alkylene alcohol group, or a fluorinated cycloalkylene alcohol group having 1 to 20 carbons; and R**° are each independently a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, a cycloalkyl group, a fluorinated cycloalkyl group, a hydroxy! group, an alkoxyl group, a fluorinated alkoxyl group, an acyl group, an acyloxy group, a fluorinated acyl group, a fluorinated acyloxy group, or any of the above groups having an amine group, or an ether group therein, with the proviso that at least one of R? and R® and at least one of R* and R°® are independently a fluorine, a fluorinated alkyl group or a fluorinated cycloalkyl group. R®and R* may be any of the groups defined for R*" and be bonded to each other to thereby form a 5 or 6 member ring including A, R® and R*. The ring may contain heteroatoms. In an alternative embodiment, both of R* and R* are fluorine, fluorinated alkyl groups or fluorinated cycloalkyl groups. In an alternative embodiment, R*" are each independently a hydrogen atom, a fluorine atom, a hydroxyl group, or comprises 1 to 20 carbons and is a fluorinated alkyl group, a fluorinated cycloalkyl group, an acyl group, an acyloxy group, a fluorinated acyl group, a fluorinated acyloxy group, an alkyl group, an alkoxy! group, a fluorinated alkoxyl group, or a cycloalkyl group (as described above.

[0024] In a further aspect of the present invention, there is provided a method for making a bridged carbocyclic compound by reacting a bridged carbocyclic reaction material and a fluorinated diol, and the methods of making and using photoresist compositions comprising bridged carbocyclic compounds are disclosed.

[0025] In yet another aspect of the present invention, there is provided a polymer comprising polymerized units of one or more bridged carbocyclic compounds of the invention. The novel polymers are transparent at wavelengths of 300 nm or less, or 200 nm or less. The novel polymers are transparent at 157 nm. The polymer has incorporated in it acidic protons to assist base solubility during the photoresist removal step prior to etching. The acidic protons can be blocked by acid labile groups. The polymers are used in photoresist compositions.

[0026] This invention further provides a bridged carbocyclic compound having the following structure:

Oo. _A_ _OR!

B”

Fe ne (1) where Ais a single bond, or a divalent organic group having 1 to 20 carbon atoms, and B is a bridged carbocyclic group of the type:

RE FR’

R10

R'? (11) wherein Z is CH,, CHR™, CR™R", CH,CH,, CH,CHR' or a heteroatom: R'is a hydrogen, fluorinated alkylene alcohol group, or a fluorinated cycloalkylene alcohol group having 1 to 20 carbons; and R*"%'2" are each independently a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, a cycloalkyl group, a fluorinated cycloalkyl group, a hydroxyl group, an alkoxy! group, a fluorinated alkoxyl group, an acyl

! group, an acyloxy group, a fluorinated acyl group, a fluorinated acyloxy group, or any of the above groups having an amine group, an ether group therein, with the proviso that at least one of R?* and R® and at least one of R* and R® is fluorine, a fluorinated alkyl group or a fluorinated cycloalkyl group. R*and R* may be any of the groups defined for R*'5 and be bonded to each other to thereby form a 5 or 6 member ring including A, R®, and

R®. The ring may contain heteroatoms. Preferably both of R® and R* are fiuorine, fluorinated alkyl groups or fluorinated cycloalkyl groups. This composition of this invention comprising Structures | and Ill will be referred to as a nortricyclane compound.

The preferred embodiments for the nortricyclane compound are the same as for the bridged carbocyciane compounds comprising Structure | and Il described in detail below, except it comprises a nortricyclane ring as shown in Structure lll, instead of the carbocyclane ring shown in Structure Il. The nortricyclane compound can be used as a dissolution inhibitor by the incorporation of a protecting group. A dissolution inhibitor is added to the photoresist composition.

[0027] These and other aspects of the invention will become apparent from the following detailed description.

DETAILED DESCRIPTION OF THE INVENTION

[0028] The present invention is directed to flucrine-containing bridged carbocyclic compounds and methods for making and using the same in, for example, a photoresist composition. The compound of the present invention may be polymerized by itself to provide a homopolymer or with other reactive monomers to provide a copolymer. The polymer of the present invention may be used, for example, in a sub-200 nm photoresist composition. The terms “resin” and “polymer” are used interchangeably throughout this specification to describe the polymer or copolymer of this invention useful in a photoresist composition.

N

[0029] The preferred method of making the compounds of this invention is by reacting bridged carbocyclic reaction material and fluorinated alcohols, preferably in a solvent, under conditions sufficient to effect a reaction to form the monomers. The bridged carbocyclic reaction materials include tetracyclo[3.2.0.0%7.0*%heptane, which is commonly referred to as quadricyclane, tetracyclo[4.2.0.0%8.0%" octane, a thioguadricyclane, an oxaquadricyclane, or a substituted derivative of quadricyclane, tetracyclo[4.2.0.0%8.0%"]octane, thioquadricyclane, or oxaquadricyclane. It was new, surprising and unexpected to produce fiuorine-containing bridged carbocyclic compounds for use as monomers (and dissolution inhibitors) for photoresist resins using those reaction materials. The resulting highly fluorinated monomers are well-suited for 157 nm or other applications.

[0030] The present invention is directed, in part, to bridged carbocyclic compounds and methods of making and using same. They may be unsaturated (one double bond in the ring) alkoxy-substituted bridged carbocyclic compounds such as ethers of bicyclo-, 18 oxabicycle, and thiabicyclo- alkenes. The compounds of the invention comprise a bridged carbocyclic ring, and an alkoxide group, wherein the oxygen of the alkoxide group is bonded to a ring member of said bridged carbocyclic ring and further wherein the carbon of said alkoxide group bonded to said oxygen further has at least one fluorine-containing group bonded to said carbon and wherein the alkoxide group has at least one hydroxyl group separated from said carbon, that is bonded to said oxygen and said fluorine-containing group, by at least one additional carbon that is bonded to said carbon that is bonded to said oxygen and to said fluorine-containing group. The alkoxide group may contain a ring. The alkoxide group may contain heteroatoms therein, such as oxygen, sulfur, a nitrogen group (e.g., N-H, N-alkyl, and N-acyl), and the like. The fluorine-containing groups include fluoroalkyl groups, fluorocyclic alkyl groups or a fluorine atom. The hydroxyl groups are hydroxyl groups preferably having a pKa < 12.

X

The carbon bonded to the —OH of the hydroxyl group may have one or two fluorine containing groups bonded thereto. As shown in Structure |, the alkoxide group includes 0, R% R% AR R°and OR’,

[0031] The preferred bridged carbocyclic compounds of this invention include: oO A OR!

Xe ne (1) where A is a single bond, or a straight chain, branched or cyclic divalent organic group having 1 to 20 carbon atoms, and can include heteroatoms such as oxygen, sulfur, a nitrogen group (e.g., N-H, N-alkyl, and N-acyl), and the like, as well as substituents such as fluorine, fluoroalkyl groups, and hydroxyl groups.

[0032] Preferably Ais a single bond, alkylene group, a hydroxyl substituted alkylene group, a fluorinated alkylene group, a hydroxyl substituted fluorinated alkylene group, a cycloalkylene group, a hydroxyl substituted cycloalkylene group, a fluorinated cycloalkylene group, or a hydroxyl substituted fluorinated cycloalkylene group with those groups having 1 to 15 carbon atoms, more preferably A is a single bond, alkylene group, a hydroxyl substituted alkylene group, a fluorinated alkylene group, a hydroxyl substituted fluorinated alkylene group, a cycloalkylene group, a hydroxyl substituted cycloalkylene group, a fluorinated cycloalkylene group, or a hydroxyl substituted fluorinated cycloalkylene group in those groups having 1 to 15 carbons. Specific examples of A include methylene; ethane-1,1-diyl (ethylidene); ethane-1,2-diyl (ethylene); propane-1,1-diyl; propane-1,2-diyl; propane-1,3-diyl; butane-1,1-diyl; butane- 1,2-diyl; butane-1,3-diyl; butane-1,4-diyl; butane-2,3-diyl; pentane-1,1-diyl; pentane-1,2- diyl; pentane-1,3-diyl; pentane-1,4-diyl; pentane-1,5-diyl; hexane-1,6-diyl; 2- methyipropane-1,2-diyl; 2-methylpropane-1,3-diyl; 3-methylbutane-1,3-diyl; 2- methylbutane-1,3-diyl; 2-methylbutane-1,4-diyl; 2,3-dimethylbutane,-2,3-diyl; 2,5-

x dimethylhexane-1,6-diyl; 3-oxapentane-1,5-diyl; cyclopropane-1,1-diyl; cyclopropane- 1,2-diyl; cyclobutane-1,1-diyl; cyclobutane-1,2-diyl; cyclobutane-1,3-diyl; cyclopentane- 1,1-diyl; cyclopentane-1,2-diyl; cylopentane-1,3-diyl; cyclohexane-1,1-diyl; cyclohexane- 1,2-diyl; cyclohexane-1,3-diyl; cyclohexane-1,4-diyl; methylcyclohexane-1,4-diyl; 1,1,2,2- tetrafluoroethane-1,2-diyl; 3,3,3-trifluoropropane-1,2-diyl; and 2-hydroxypropane-1,3-diyl;

HO. CF3 cand CFs CFs CFs

[0033] Bis a bridged carbocyclic group of the type.

R® 7

R10

RT R™ an)

[0034] wherein Z is CH, CHR'®, CR™R", CH,CH,, CH,CHR' or a heteroatom, for example, oxygen, a nitrogen group (e.g., N-H , N-alkyl, and N-acyl) or sulfur, preferably Z is oxygen or CH;, more preferably Z is CH.

[0035] R'is a hydrogen, a fluorinated alkylene alcohol group having 1-20 carbons, or a fluorinated cycloalkyiene alcohol group having 1-20 carbons, preferably R'is hydrogen.

R%'S are each independently a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, a cycloalkyl group, a hydroxyl group, a fluorinated cycloalkyl group, a hydroxyl group, an alkoxy! group, a fluorinated alkoxy! group, an acyl group, a fluorinated acyl group, an acyloxy group, a fluorinated acyloxy group, or any of the above groups having an amine group, or an ether group therein, wherein the alkyl group, fluorinated alkyl group, cycioalky! group, fluorinated cycloalkyl group, acyl group, fluorinated acy! group, acyloxy group, fluorinated acyloxy group, alkoxyl group, or fluorinated alkoxyl group comprises from 1 to 20 carbons; with the proviso that at least x one of R? and R® and at least one of R* and R® is a fluorine, a fluorinated alkyl group or a fluorinated cycloalkyl group. R® and R* may also be joined within their structures to form 2 ew a ring, as illustrated by HO CHa . Preferably both R® and R* are fluorine, fluorinated alkyl groups or fluorinated cycloalkyl groups.

[0036] Preferably, R*" are each independently a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, a cycloalkyl group, a fluorinated cycloalkyl group, a hydroxy! group, an alkoxyl group, a fluorinated alkoxyl group, wherein the alkyl group, the fluorinated alkyl group, cycloalkyl group, fluorinated cycloalkyl group, alkoxyl, or fluorinated alkoxyl group comprises from 1 to 20 carbons, more preferably 1 to 10 carbons.

[0037] Preferably R'*" are each independently a fluorinated cyclo atkyl group having 1-10 carbons, a tluorinated alkyl group having 1-10 carbons, or a fluorine atom.

[0038] Preferably R®’ are each independently a fluorinated alkyl having 1-10 carbons, a fluorinated alkoxy group having 1-10 carbons, a hydrogen atom or a fluorine atom, more preferably both R® and R’ are hydrogen atoms.

[0039] Preferably R82 are each independently a fluorinated alkyl having 1-10 carbons, fluorinated alkoxy having 1-10 carbons, a hydrogen atom or a fluorine atom, more preferably all of R*'? are hydrogen atoms.

[0040] In some embodiments R'is a hydrogen, R*and R® are each independently a fluorinated alkyl groups having 1 to 5 carbons, a fluorinated cyclic alkyl group having 1 to 5 carbons or a fluorine atom. In an alternative embodiment R' is a hydrogen, and R?, R®,

R*and R® are —CF3. In the preferred embodiments, B is norbornenyl, or 7-

R oxanorbornenyl, preferably norbornenyl. The preferred fluorinated monomers of this invention have seven or more fluorine atoms, more preferable from nine to thirty-five fluorines , most preferably between from twelve to thirty fluorine atoms present on the fluorinated alcohol monomer molecule.

[0041] In some embodiments of the present invention, there is provided a norbornene compound of the formula (IV):

Oo A OH (IV)

[0042] where A and R?® are as defined above. More preferably, A is a single bond or any linear or branched alky! group having 1 tc 6 carbons, or fluorinated alkyl group having 1 to 15 carbons, or cycloalkyl group having 4 to 6 carbons, or fluorinated cycloalkyl group having 4 to 6 carbons, and where R? is a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbons, a fluorinated alkyl group having 1 to 6 carbons, a cycloalkyl group having 4 to 6 carbons, or a fluorinated cyclo alkyl group having 4 to 6 carbons, and R¥s are independently fluorinated alkyl groups having 1 to 3 carbons or fluorinated cycloalkyl groups having 1 to 3 carbons. Most preferred, A is a single bond or any linear or branched alkyl group having 1 to 6 carbons or fluorinated alkyl group having 1 to 15 carbons or cycloalkyl group having 4 to 6 carbons or fluorinated cycloalkyl group having 4 to 6 carbons, and where R*®° are independently fluorinated alkyl groups having 1 to 3 carbons or a fluorinated cycloalkyl group having 1 to 3 carbons.

[0043] The term “alkyl” as used herein includes straight chain or branched groups, preferably containing from 1 to 20 carbon atoms, or more preferably from 1 to 10 carbon atoms. Exemplary alkyl groups include methyl, ethyl, n-propyl, isopropyl, n-butyl, isobutyl, sec-butyl, tert-butyl, tert-amyl, n-pentyl, and n-hexyl. The term “fluorinated” applies to moieties wherein one or more of its hydrogens are replaced by a fluorine atom,

“ and may be partially or fully fluorinated.

In certain embodiments, some of the alkyl groups may be substituted with one or more heteroatoms, such a halogen atom, or other heteroatoms such as O, N, or S.

The term “cycloalkyl” refers to a cyclic alkyl structure, preferably containing from 3 to 20 carbon atoms e.g. cyclopentyl, or cyclohexyl, and fluorinated cycloalkyl applies to cycloalkyl moieties in which one or more of its hydrogens are replaced by a fluorine atom, and may be partially or fully fluorinated. in certain embodiments, some of the cycloalkyl groups may be substituted with a halogen or with one or more heteroatoms, such as O, N, or S.

The term “alkoxy!” refers to a group having the following structure R’-O, where R' is an alkyl or cycloalkyl group as defined above including fluorinated derivatives thereof.

Claims (39)

\ CLAIMS

1. A bridged carbocyclic compound comprising a bridged carbocyclic ring, and an alkoxide group, wherein an oxygen of the alkoxide group is bonded to a ring-member of said bridged carbocyclic ring and to a carbon of the alkoxide group, and further wherein the carbon of the alkoxide group bonded to said oxygen has at least one fluorine-containing group bonded to said carbon and further wherein said alkoxide group has at least one hydroxyl group separated from said carbon that is bonded to said oxygen and said fluorine-containing group by at least one additional carbon that is bonded to said carbon that is bonded to said oxygen.

2. The bridged carbocyclic compound of claim 1, having the following structure:

o. _A_ _OR' 5 Ie RRR" R 0) wherein A is a single bond, or a divalent organic group having 1 to 20 carbon atoms, and B is a bridged carbocyclic group of the type: RE 7 RO RT R'™2 a wherein Z is CH,, CHR, CR™R', CH,CH,, CH,CHR™ or a heteroatom; R' is a hydrogen, fluorinated alkylene alcohol group having 1 to 20 carbons, or a fluorinated cycloalkylene alcohol group having 1 to 20 carbons; and R%*'® are each independently a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, a cycloalkyl group, a fluorinated cycloalkyl group, a hydroxyl group, an alkoxy! group, a fluorinated -B7 -

\ alkoxyl group, an acy! group, an acyloxy group, a fluorinated acyl group, a fluorinated acyloxy group, or any of said groups having an amine group, or an ether group therein, and R® and R* may be bonded together to form a portion of a five or six member ring which may contain heteroatoms, with the proviso that at least one of R? and R® and at least one of R* and R® are independently a fluorine, a fluorinated alkyl group or a fluorinated cycloalkyl group.

3. The compound of claim 2, wherein R*'° are each independently a hydrogen atom, a fluorine atom, a hydroxy! group, or comprises 1 to 20 carbons and is an alkyl group, a fluorinated alkyl! group, a cycloalkyl group, a fluorinated cycloalkyl group, an alkoxyl group, a fluorinated alkoxyl group, an acyl group, an acyloxy group, a fluorinated acyl group, a fluorinated acyloxy group, or any of said groups having an amine group, or an ether group therein.

4. The compound of claim 2, wherein R* and R* are independently a fluorine atom, a fluorinated alkyl! group or a fluorinated cycloalkyl group.

5. The compound of claim 2, wherein A is a single bond or comprises 1 to 15 carbons and is an alkylene group, a hydroxyl substituted alkylene group, a fluorinated alkylene group, a hydroxyl substituted fluorinated alkylene group, a cycloalkylene group, a hydroxy! substituted cycloalkyiene group, a fluorinated cycloalkylene group, or a hydroxyl substituted fluorinated cycloalkylene group.

6. The compound of claim 2 wherein A is a single bond, or comprises 1 to 10 carbons and is an alkylene group, a hydroxyl substituted alkylene group, a fluorinated alkylene group, a hydroxyl substituted fluorinated alkylene group, a cycloalkylene group,

\ a hydroxy! substituted cycloalkylene group, a fluorinated cycloalkylene group, or a hydroxy! substituted fluorinated cycloalkylene group.

7. The compound of claim 2 wherein A is selected from the group consisting 5S of methylene; ethane-1,1-diyl (ethylidene); ethane-1,2-diyl (ethylene); propane-1,1-diyl; propane-1,2-diyl; propane-1,3-diyl; butane-1,1-diyl; butane-1,2-diyl; butane-1,3-diyl; butane-1,4-diyl; butane-2,3-diyl; pentane-1,1-diyl; pentane-1,2-diyl; pentane-1,3-diyl; pentane-1,4-diyl; pentane-1,5-diyl; hexane-1,6-diyl; 2-methylpropane-1,2-diyl; 2- methylpropane-1,3-diyl; 3-methylbutane-1,3-diyl; 2-methylbutane-1,3-diyl; 2- methylbutane-1,4-diyl; 2,3-dimethylbutane,-2,3-diyl; 2,5-dimethylhexane-1,6-diyl; 3- oxapentane-1,5-diyl; cyclopropane-1,1-diyl; cyclopropane-1,2-diyl; cyciobutane-1,1-diy}; cyclobutane-1,2-diyl; cyclobutane-1,3-diyl; cyclopentane-1,1-diyl; cyclopentane-1,2-diyl; cylopentane-1,3-diyl; cyclohexane-1,1-diyl; cyciohexane-1,2-diyl; cyclohexane-1,3-diyl; cyclohexane-1,4-diyl; methylcyclohexane-1,4-diyl; 1,1,2,2-tetrafluoroethane-1,2-diyl; Ho CFs 3,3,3-trifluoropropane-1,2-diyl; and 2-hydroxypropane-1,3-diyl; ; and OH CHj YT CFs CF3 CF3

8. The compound of claim 2, wherein Z is selected from the group consisting of oxygen, a nitrogen group, sulfur, and CH,.

9. The compound of claim 2, wherein Z is CH.

\

10. The compound of claim 2 wherein RZ" are each independently a hydrogen atom, a fluorine atom, a hydroxyl group, or comprises 1 to 20 carbons and is an alkyl group, a fluorinated alkyl group, a cycloalkyl! group, a fluorinated cycloalkyl group, an alkoxyl! group, or a fluorinated alkoxy! group. c

11. The compound of claim 2 wherein R*'?are each independently a fluorinated alkyl having 1 to 10 carbons, a fluorinated alkoxy group having 1 to 10 carbons, a hydrogen atom or a fluorine atom.

12. The compound of claim 2 wherein R'is a hydrogen, R*and R® are each independently a fluorinated alkyl group having 1 tc 5 carbons, a fluorinated cyclic alkyl group having 1 to 5 carbons or a fluorine atom.

13. The compound of claim 2 wherein R' is a hydrogen, and R?, R®, R*and R® are CFs.

14. The compound of claim 2 wherein B is norbornenyl, or 7-oxanorbornenyl.

15. The compound of claim 2 wherein said compound comprises seven or more fluorine atoms.

16. The compound of claim 2 comprising the following structure: yr ol RZR*R' R® (IV)

\

17. The compound of claim 16, wherein A is a single bond or any linear or branched alkyl group having 1 to 6 carbons, or fluorinated alkyl group having 1 to 15 carbons, or cycloalkyl group having 4 to 6 carbons, or fluorinated cycloalkyl group having 4 to 6 carbons, and wherein R? is a hydrogen atom, a fluorine atom, an alkyl group having 1 to 6 carbons, a fluorinated alkyl group having 1 to 6 carbons, a cycloalkyl group having 4 to 6 carbons, or a fluorinated cyclo alkyl group having 4 to 6 carbons, and R>* are each independently a fluorinated alkyl group having 1 to 3 carbons or a fluorinated cycloalkyl group having 1 to 3 carbons.

\

18. The compound of claim 16, selected from the group consisting of: F4C CF; 3-bicyclo[2.2.1}hept-5-en-2-yloxy-2,3- 0 } { OH bis(trifluoromethyl)-1,1,1,4.4,4- EC oF hexafluorobutan-2-ol 3 3 F3C 4-bicyclo[2.2.1]hept-5-en-2-yloxy-2,4- 0 bis(trifluoromethy!)-1,1,1,5,5,5- hexafluoropentan-2-ol F5C CFj, FC OH 5-bicyclo[2.2.1]hept-5-en-2-yloxy-2,5- F1C 0 CE bis(trifluoromethyl)-1,1,1,6,6,6- 3 hexafluorohexan-2-ol F3C OH CF; F3C 6-bicyclo[2.2.1]hept-5-en-2-yloxy-2,6- 0 bis(trifluoromethyl)-1,1,1,7,7,7- EC hexafluoroheptan-2-ol 3 CF4 FC OH FaC 7-bicyclo[2.2.1]hept-5-en-2-yloxy-2,7- G bis(trifluoromethyl)-1,1,1,8,8,8- gy CE hexafluorooctan-2-ol x) 3 OH CF; FaC 6-bicyclo[2.2.1]hept-5-en-2-yloxy-2,6- o bis(trifluoromethyl)-1,1,1,7,7,7-hexafluoro-

F.C 4-methytheptan-2-ol CF F4sC OH

Y - 4-bicyclo[2.2.1]hept-5-en-2-yloxy-3,4- Sa Con bis(trifluoromethyl)-1,1,1,2,2,5.5,6,6,6- Fal CEs decafluorchexan-3-ol FaCF2C 5-bicyclo[2.2.1]hept-5-en-2-yloxy-3,5- fie bis(trifluoromethyl)-1,1,1,2,2,6,6,7,7,7- FC CR-CFR decafluorcheptan-3-ol FC OH FaCFoC 6-bicyclo[2.2.1]hept-5-en-2-yloxy-3,6- A CE-CF bis(trifluoromethyl)-1,1,2,2,7,7,8,8,8- FiC oH nonafluorooctan-3-ol Ch : FaCFaC 7-bicyclo[2.2.1}hept-5-en-2-yloxy-3,7- Ae bis(trifluoromethyl)-1,1,1,2,2,8,8,9,9,9- Fal decafluorononan-3-ol ChCR Fi OH F3CF.C 8-bicycio[2.2.1]hept-5-en-2-yloxy-3,8- Ne bis(trifluoromethyl)-1,1,1,2,2,9,8,10,10,10- FaC CRC decafluorodecan-3-ol 0H CFa FCFC 7-bicyclo[2.2.1]hept-5-en-2-yloxy-3,7- pe bis(trifluoromethyl)-1,1,1,2,2,8,8,9,9,9- FC decafluoro-5-methyinonan-3-ol ChaCha FC OH

\ (F3CRFC CF,CFs 4-bicyclo[2.2.1]hept-5-en-2-yloxy-3,4- or—E-o bis[1,2,2,2-tetrafluoro-1- CF3FC CF(CFa), (trifluoromethyl)ethyl]-1,1,1,2,2,5,5,6,6,6- B ” decafluorohexan-3-ol (F3ChFC 5-bicyclo[2.2.1]hept-5-en-2-yloxy-3,5- in bis[1,2,2,2-tetrafluoro-1- FaCFaC CF(CFsk (trifluoromethyl)ethyl}-1,1,1,2,2,6,6,7,7,7- F2CF,C OH decafluoroheptan-3-al (FCpFC B-bicyclo[2.2.1]hept-5-en-2-yloxy-3,6- — CF{CF3h bis[1,2,2,2-tetrafluoro-1- FaCF.C OH (trifluoromethyl)ethyl]-1,1,1,2,2,7,7,8,8,8- CF,CFa decafluorooctan-3-ol {FaCpFC 7-bicyclo[2.2.1]hept-5-en-2-yloxy-3,7- oo bis[1,2,2,2-tetrafluoro-1- F3CF,C (triffluoromethyl)ethyl]-1,1,1,2,2,8,8,9,9,9- CFaCFy decafiuorononan-3-ol {rC)RFC OH (F2ChFC 8-bicyclof2.2.1]hept-5-en-2-yloxy-3,8- A bis[1,2,2,2-tetrafluoro-1- . CF.CF (trifluoromethyl)ethyl]- FaCRC 2s 1,1,1,2,2,9,9,10,10,10-decafluorodecan-3- Ci ol CHCk (F-ChFC 7-bicyclof2.2.1]hept-5-en-2-yloxy-3,7- ie bis[1,2,2,2-tetrafluoro-1- F4CELC are uoromethyjeinil-) ,1,1,2,2,8,8,9,9,9- CFCFsh ecafiuoro-5-methylnonan-3-ol FiCFC OH

{ 7-bicyclo[2.2.1]hept-5-en-2-yloxy-3,7- F3C bis(trifluoromethyl)-1,1,1,2,2,8,8,8- 9) octafluoro-5-methyloctan-3-ol

F.C CF,CF, FsC OH FC 7-bicyclo[2.2.1]hept-5-en-2-yloxy- 3=, 1,1,1,2,2,8,8,8-octafluoro-5-methyl-3- J O [1,2,2,2-tetrafluoro-1- F3C (trifluoromethyl)ethyl}-7- trifluoromethyl)octan-3-ol CF(CF)y 4 F3CF,C OH 7-bicyclo[2.2.1]hept-5-en-2-yloxy- NG 2 1,1,1,2,2,8,8,9,9,9-decafluoro-5-methyl-3- 7 7 0 [1,2,2,2-tetrafluoro-1- J Bl =Ne, (triflucromethyi)ethyl]-7- N trifluoromethyl)nonan-3-ol CFCFa) | Y F3CF,C OH HiC B-bicyclo[2.2.1]hept-5-en-2-yloxy- 0 1,1,1,7,7,7-hexafluoro-4,6-dimethyl-2- (trifluoromethyl)heptan-2-ol F3C SE FC OH

H.C 7-bicyclo[2.2.1]hept-5-en-2-yloxy- Io) 1,1,1,2,2,8,8,8-octafluoro-5,7-dimethyl-3- 3 Na (trifluoromethyl)octan-3-ol F2C SN CFaCrs FC OH \ HsC 7-bicyclo[2.2.1]hept-5-en-2-yloxy- - \ 1,1,1,2,2,8,8,8-octafluoro-5,7-dimethyl-3- SNS [EIR Eat ht hg] 1 y ie, OF [1,2,2,2-tetrafluoro-1- FiC JN (trifluoromethyl)ethylloctan-3-ol Py CHCFa) F,CFC OH

2-{3-[1-bicyclo[2.2.1]hept-5-en-2~yloxy- 0 = 2,2,2-trifluoro-1- : 3 (triftuoromethyl)ethyl]cyclohexyl}~ CFs 1,1,1,3,3,3-hexafluoropropan-2-ol Ch OH Ch 2-{3-[1-bicyclo[2.2.1]hept-5-en-2-yloxy- 2,2,3,3,3-pentafluoro-1- Ss O SESE (trifluoromethyl) propyijcyclohexyl}- : Ck, 1,1,1,3,3,4,4,4-octafluorobutan-2-of : CHCF5 OH Ck, 3-(3-{1-bicyclo[2.2.1]}hept-5-en-2-yioxy- OG, CRCF; 2,2,3,3,3-pentafluoro-1-[1,2,2,2- CF tetrafluoro-1- {Chk (trifiucromethyl)ethyl]propyl}cyciohexyl)- 1,1,1,2,4,4,5,5,5-nonafluoro-2- : (trifluoromethyl)pentan-3-ol OH CHCF3) \ 2-{3-[1-bicyclo[2.2.1]hept-5-en-2-yloxy- a 2,2,2-trifluoro-1- ~~ { = er Ao <C 3 (trifluoromethyl)ethyl]cyciohexyl}- CFs 1,1,1,3,3,4,4,4-octaflucrobutan-2-ol @X CRaCh5 To CF,

3-{3-[1-(Bicyclo[2.2.1]hept-3-en-2-yloxy)- 0 CF 2,2, 2-trifluoro-1-trifluoromethyl-e thyi)- 3 cyclohexyl}-1,1,1,2,2,4,5,5,5-nonafluoro- Ch3 4-trifluoromethyl-pentan-3-ol CFoLCF3 OH CHCF3) 3-{3-[1-(Bicyclo[2.2.1]hept-5-en-2-yloxy)- g 8) £ 2,2,3,3,3-pentafluoro-1-trifluoromethyl- Na CFCs propyl]-cyciohexyl}-1,1,1,2,2,4,5,5,5- Ck, nonafluoro-4-trifiuoromethyl-pentan-3-ol CrCR3 OH CHCR3)y

\

F.C OH 4-[2-bicyclo[2.2.1]hept-5-en-2-yloxy- : 3 3,3,3-trifluoro-2-(trifluoromethyl)- Chi propyl]-2,6-bis(trifluoromethyl)- 1,1,1,7,7,7-hexafluoroheptane-2,6-diol FsC 0 CFs F3C FC OH CE 4-[5-bicyclo[2.2.1]hept-5-en-2-yloxy- bH 6,6 6-trifluoro-3-methyi-5- (trifluoromethyl)hexyl]-2,6- CFs bis(triflucromethyl)-1,1,1,7,7,7- fo hexafluoroheptane-2,6-diol F3C CF3 F3C Chk, OH CF 4-[2-bicyclo[2.2.1]hept-5-en-2-yloxy- by 3,3, 3-trifluoro-2-(trifluoro- methyl)propyl]-2,9-bis(trifluoromethyl)- CFs 1,1,1,10,10,10-hexafluoro- > 0 7-methyldecane-2,9-diol FaC CFs HO FiC CFs 6-bicyclo[2.2.1]hept-5-en-2-yloxy-

O . 1,1,1,7,7,7-hexafluoro-2-methyl-4- Chi (trifluoromethyl)heptane-2,4-diol Ck; OH CF3 H,C OF 0 CE. 4-bicyclo[2.2.1]hept-5-en-2-yloxy-6- = "3 methyl-2,4,6-tris(trifluoromethyl)-2H- 3,4,5,6-tetrahydropyran-2-ol CFs HO O CHa CFj

\ Ho [2 FaC F3C on Me FiC CF,

19. A compound comprising the following structure : OH

20. The bridged carbocyclic compound of claim 1 comprising the following structure: _o_ _A_ _OR 0) wherein A is a single bond, or a divalent organic group having 1 to 20 carbon atoms, and B is a bridged carbocyclic group of the type: RE FR R10 R'2 (Ii) wherein Z is CH,, CHR? CR"R"™, CH,CH,, CH,CHR" or a heteroatom; R'is a hydrogen, fluorinated alkylene alcohol group, or a fluorinated cycloalkylene alcohol group having 1 to 20 carbons; and R*'*'?'° are each independently a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, a cycloalkyl group, a fluorinated cycloalkyl group, a hydroxyl group, an alkoxyl group, a fluorinated alkoxyl group, an acy! group, an acyloxy group, a fluorinated acyl group, a fluorinated acyloxy group, or any of the said groups having an amine group, an ether group therein, and R% and R* may be bonded together to form a portion of a five or six member ring which may contain

\ heteroatoms, with the proviso that at least one of R? and R? and at least one of R* and R® are independently a fluorine, a fluorinated alkyl group or a fluorinated cycloalkyl group.

21. A method of making a bridged carbocyclic compound comprising the steps of: combining a bridged carboxylic reaction material and a fluorinated alcohol to form a reaction mixture and reacting said bridged carboxylic reaction material and said fluorinated alcohol to produce said bridged carbocyclic compound.

22. The method of claim 21 wherein said carboxylic reaction material is selected from the group consisting of quadricyclane, tetracyclo[4.2.0.0%%.0%"Joctane, thioquadricyclane, oxaquadricyclane, or substituted derivative of quadricyclane, tetracyclo[4.2.0.0%%.0°"Joctane, thioquadricyclane, or oxaquadricyclane.

23. The method of claim 21 wherein said fluorinated alcohol and said bridged carbocyclic reaction material are combined in a molar ratio between from 1:1 to 3:1.

24. The method of claim 21 wherein said reaction mixture further comprises a solvent selected from the group consisting of an ether solvent, an aromatic solvent, a nitrile, or an alkyl alcohol, or mixtures of said solvents.

25. The method of claim 21 wherein said reaction mixture further comprises an acid or an acid catalyst.

\

26. The method of claim 21 further wherein said reacting step produces an isomer of said bridged carbocyclic compound.

27. The method of claim 21 wherein the fluorinated alcohols have the following structural formula: HO A OH wherein A is a single bond, or a divalent organic group having 1 to 20 carbon atoms, R?, R3 R* and R®are each independently a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, a cycloalky! group, a fluorinated cycloalkyl group, a hydroxyl group, an alkoxyl group, a fluorinated alkoxyi group, an acyl group, an acyloxy group, a fluorinated acyl group, a fluorinated acyloxy group, or any of said groups having an amine group, or an ether group therein, and R3 and R* may be bonded together to form a portion of a five or six member ring which may contain heteroatoms, with the proviso that at least onc of R? and R® and at least one of R* and R® is fluorine, a fluorinated alkyl group or a fluorinated cycloalkyl group.

\

28. The method of claim 21 wherein said fluorinated alcohols are selected from the group consisting of: FaC CF 2,3-bis(trifluoromethyl)-1,1,1,4,4 4- 3 3 hexafluorobutane-2,3-diol opr FC CF, E+C 2,4-bis(trifluoromethyl)-1,1,1,5,5,5- 3 hexafluoropentane-2,4-diol HO F1C CFs FC OH FsC 2 >-bis(trifluorometry)- 1 ,1,6,6,6- exafluorohexane-2,5-dio HO Cha FC OH Cry Fal 2,6-bis(trifluoromethyl)-1,1,1,7,7,7- H 3 hexafluoroheptane-2,6-diol FC Ck, FaC OH F3C 2,7-bis(trifluoromethyl)-1,1,1,8,8,8- hexafiuorooctane-2,7-diol HO FC Se — CH CFs 2,6-bis(trifluoromethyl)-1,1,1,7,7,7- FS hexafluoro-4-methylheptane-2,6-diol HO—Z=— FaC —\ RCE

F.C OH

3,4-bis(trifluoromethyl)-1,1,1,2,2,5,5,8,6,6- FCC CCH decafluorohexane-3,4-diol YL FC CH 3,5-bis(trifluoromethyl)-1,1,1,2,2,6,6,7,7,7- ESE decafluoroheptane-3,5-diol FC CCF FC OH 3,6-bis(trifluoromethyl)-1,1,1,2,2,7,7,8,8- FLRC nonafluorooctane-3,6-diol CECE; FC OH Cks — 3,7-bis(trifluoromethyl)-1,1,1,2,2,8,8,9,9,9- ESE decafluorononane-3,7-diol FC CCR FC OH 3,8-bis(trifluoromethyl)- FCC 1.1,1,2,2,9,9,10,10,10-decafluorodecane- HO 3,8-diol FaC CFCs OH Chs FACFaC 3,7-bis(trifluoromethyl)-1,1,1,2,2,8,8,9,9,9- ha decafluoro-5-methyinonane-3,7-diol FC ChHCH F<C CH

( 3,4-bis[1,2,2,2-tetrafluoro-1- F3CFC CFCF3 (trifluoromethyl)ethyi}-1,1,1,2,.2,5,5.,6,6,6- HO——{-oH decafluorohexane-3,4-diol (CR3RpFC CHCF3h

E.CLFC 3,5-bis[1,2,2,2-tetrafluoro-1- (F3ChF (trifluoromethyl)ethyl]-1,1,1,2,2,6,6,7,7,7- HO decafluoroheptane-3,5-diol FsCFC CF(CF3) F2CEC OH 3,6-bis[1,2,2,2-tetrafluoro-1- (FCRFG (trifluoromethyl)ethyl}-1,1,1,2,2,7,7.8.8,8- H CHCFsh decafluorooctane-3,6-diol FCC OH CFCF3 F3CF,C 3,7-bis[1,2,2,2-tetrafluoro-1- (trifluoromethyl)ethyl]-1,1,1,2,2,8,8,9,9,9- HO decafiuorononane-3,7-diol FCRC ChoCha (FRCpFC OH c 3,8-bis[1,2,2,2-tetrafluoro-1- (FaCRFC (trifluoromethyi)ethyi]- H 1,1,1,2,2,9,9,10,10,10-decafluorodecane- F3CF.C CF.CR3 3,8-diol OH CHCRF3h ~ 3,7-bis[1,2,2,2-tetrafluoro-1- 2 i 14-9 (Falk (triffluoromethyl)ethyl]-1,1,1,2,2,8,8,9,9,9- HO decafluoro-5-methylnonane-3,7-diol F4CFC CHCF3) r3CFC OH

F3C : 2,6-bis(trifluoromethy!)-1,1,1,7,7,8,8,8- : octafluoro-4-methyloctane-2,6-diol HO FiC N CF,CF3 FC OH

F.C 1,1,1,7.7,8,8,8-octafluoro-4-methyl-6- ™ {1,2,2,2-tetrafluoro-1- (trifluoromethyl) ethyl}- HO 2-(trifluoromethyljoctane-2,6-diol FC CF(CFa)h FaCF,C OH F3CF2C 1,1,1,2,2,8,8,9,9,9-decafluoro-5-methyl-3- oN [1,2,2,2-tetrafluoro-1-(triflucromethyl)ethyl]- HO 7-(trifluoromethyl)nonane-3,7-diol FaC »—CF(CF3) FL,CF,C OH HC 1,1,1,7.7,7-hexafluoro-2,4-dimethyl!-6- N (trifluoromethyl)heptane-2,6-diol HO—3— FC \ NSF FiC OH

H.C 1,1,1,7,7,8,8,8-octafiuoro-2,4-dimethyl-6- HO ; . (trifluoromethyl)octane-2,6-diol FiC J N / —CFyCF;

F.C OH

H.C 1,1,1,7,7,8,8,8-octafiuoro-2,4-dimethyl-6- STN (1,2,2,2-tetrafluoro-1- HO7\ (trifluoromethyl)ethyl]octane-2,6-diol F,C TN / }—CF(CFij F;CrHC OH

{ . HO CF ! ,1,3,3,3-hexafluoro-2-{3-{2,2,2-trifluoro- -hydroxy-1- CFs (trifluoromethyl)ethyl]cyclohexyl}propan-2- ol CFs OH CFs HO CF4CF3 1,1,1,3,3,4,4,4-octafluoro-2-{3-[2,2,3,3,3- < pentafluoro-1-hydroxy-1- Crs (trifluoromethyl) propyl]cyclohexyl}butan-2- ol OH CFa HO CE-CF 1,1,1.2,4,4,5,5,5-nonafluoro-3-(3- ~ 2 "3 {2,2,3,3,3-pentafluoro-1-hydroxy-1- Cr{Crak2 [1,2,2,2-tetrafluoro- 1(trifluoromethyl)ethyllpropyt}cyclohexyl)-2- (trifluoromethyl)pentan-3-ol CFCF3 OH CF{CF3)2 1,1,1,3,3,4,4 4-octafluoro-2-{3-[2,2,2- HO CFs trifluoro-1-hydroxy-1- CFs (trifluoromethyl)ethyl]cyclohexyl}butan-2-ol CF3CF3 OH Cky 1,1,1,2,2,4,5,5,5-nonafluoro-3-{3-[2,2,2- HO CFs trifluoro-1-hydroxy-1- CFs (trifluoromethyl)ethyljcyclohexyl}-4- (trifluoromethyl)pentan-3-ol CFoCF3 CH CF(CFa»n

{ HO CF-CF> 1,1,1,2,2,4,5,5,5-nonafluoro-3-(3- <0 [2,2,3,3,3-pentafluoro-1-hydroxy-1- CFs (trifluoromethyl)propyl]cyclohexyl}-4- (trifluoromethyl)pentan-3-ol CFyCF3 OH CF(CFap 2,6-bis(trifluoromethyl)-1,1,1,7,7,7- HO CFs hexafluoro-4-[3,3, 3-trifluoro-2-hydroxy-2- F3C (trifluoromethyl)propyl]heptane-2,6-diol CF3 FaC OH HO CFj3 CFa HO CF4 2,9-bis(trifluoromethyl)-1,1,1,10,10,10- FaC hexafluoro-4-methyl-7-[3,3,3-trifluoro-2- hydroxy-2-(trifluoromethyl)propyljdecane- 2,9-diol FsC OH FaC CFs HO CFs OH 1,1,1,7,7,7-hexafluoro-2-methyl-4- CFa (trifluoromethyl)heptane-2,4,6-triol HO CH, F3C”~ HO CF, HO CF 6-methyl-2,4 6-tris(trifluoromethyl)-2H-

3.,4,5,6-tetrahydropyran-2,4-diol Crq HO | =” “CHa a

29. The method of claim 21 wherein after said reacting step, the method further comprises the step of polymerizing said bridged carbocyclic compound.

30. A method of polymerizing a bridged carbocyclic compound to form a polymer comprising the step of combining a metal catalyst, a molecular weight modifier and a bridged carbocyclic compound, wherein said bridged carbocyclic compound

\ comprises a bridged carbocyclic ring, and an alkoxide group, wherein an oxygen of the alkoxide group is bonded to a ring-member of said bridged carbocyclic ring and to a carbon of the alkoxide group, and further wherein the carbon of the alkoxide group bonded to said oxygen has at least one fluorine-containing group bonded to said carbon and further wherein the alkoxide group has at least one hydroxyl group separated from said carbon that is bonded to said oxygen and said fluorine-containing group by at least one additional carbon that is bonded to said carbon that is bonded to said oxygen. : 31. The method of claim 30 wherein said molecular weight modifier is ethyl acetate.

32. A polymer comprising polymerized units of a bridged carbocyclic compound comprising a bridged carbocyclic ring, and an alkoxide group, wherein an oxygen of the alkoxide group is bonded to a ring-member of said bridged carbocyclic ring and to a carbon of the alkoxide group, and further wherein the carbon of the alkoxide group bonded to said oxygen has at least one fluorine-containing group bonded to said carbon and wherein the alkoxide group has at least one hydroxy! group separated from said carbon that is bonded to said oxygen and said fluorine-containing group by at least one additional carbon that is bonded to said carbon that is bonded to said oxygen.

33. The polymer of claim 32 wherein said polymerized units comprise the following formula:

\ Heh NF RS A R* A R® OR’ v) wherein A is a single bond, or a divalent organic group having 1 to 20 carbon atoms, and B' is a bridged carbocyclic group of the type: RS R’ RIC rR! R12 vi) wherein Z is CH, CHR'®, CR"R™, CH,CH,, CH,CHR' or a heteroatom; R' is a hydrogen, fluorinated alkylene alcohol group, or a fiuorinated cycloalkylene alcohol group having 1 to 20 carbons; and R?" are each independently a hydrogen atom, a fluorine atom, an alkyl group, a fluorinated alkyl group, a cycloalkyl group, a fluorinated cycloalkyl group, a hydroxy! group, an alkoxyl group, a fluorinated alkoxyl group, an acyl group, an acyloxy group, a fluorinated acyl group, a fluorinated acyloxy group, or any of said groups having an amine group, or an ether group therein, and R® and R* may be bonded together to form a portion of a five or six member ring which may contain heteroatoms, with the proviso that at least one of R? and R® and at least one of R* and R® are independently a fluorine, a fluorinated alkyl group or a fluorinated cycloalkyl group, and n is 3 to 500.

34. The polymer of claim 32 further comprising polymerized units of at least one other ethylenically unsaturated monomer.

\

35. The polymer of claim 34 wherein said ethylenically unsaturated monomers are selected from the group consisting of C4-C4g alkyl (meth)acrylate monomers, vinyl aromatic monomers, vinyl esters, vinyl-unsaturated carboxylic acids monomers, nitrogen- containing vinyl unsaturated monomers, dienes, ethylene, norbornene, hydroxyethyl(meth)acrylate, hydroxypropyl(meth)acrylate, fluorinated olefins, partially and fully fluorinated derivatives of propylene, butylene, and isobutylene, fluorinated derivatives of maleic anhydride, fluoro- (meth)acrylates (vinyl substituted), and fiuoro- methacrylates (methyl substituted), and fluorovinyl ethers, CF Are a Ler FaC OH FsC = os bor

36. The polymer of claim 34 wherein said ethylenically unsaturated monomer comprises acid-labile groups selected from the group consisting of tertiary alkoxy groups, tert-alkoxycarbonyl groups, alkoxy methyl groups, cyclic derivatives of alkoxy methyl groups.

37. The polymer of claim 34 used in a photoresist composition.

38. A method of creating a patterned image on a substrate to form a circuit component comprising: applying a photoresist composition comprising the polymer of claim 32 to a substrate and exposing said photoresist composition to energy to produce a patterned image on said substrate.

39. A compound according to claim 1 as specifically described herein.

DATED THIS 20TH DAY OF JULY 2004 SPOOR & FISHER APPLICANTS PATENT ATTORNEYS