Radiation durable organic compounds with high transparency in the vacuum ultraviolet, and method for preparing

A process for preparing an organic composition characterized by an absorbance/micrometer of <1 at wavelengths from 140 to 260 nm, comprising subjecting to treatment with one or more means for extracting one or more photochemically active species, a compound selected from the group consisting of:

• i) cyclic, linear, or branched hydrofluorocarbons having 2 to 10 carbon atoms in which there are more fluorines than hydrogen, no runs of adjacent C—H bonds longer than two (CH—CH), no runs of adjacent C—F bonds longer than 6 (CF—CF—CF—CF—CF—CF), and no —CH2CH3 radicals;
• ii) X—Rfa[ORfb]nORfcY wherein X and Y can be hydrogen or fluorine and Rfa, Rfb, and Rfc are 1 to 3 carbon fluorocarbon radicals, linear or branched
• in which there are more fluorines than hydrogens, no runs of adjacent C—H bonds longer than two are present, no —CH2CH3 radicals are present and no sequences with hydrogen on both sides of an ether oxygen (CH—O—CH) are present;
• iii) CnF2n−v+2Hv wherein n=2 to 10, v<n+1, no runs of adjacent C—H bonds longer than two are present, no runs of adjacent C—F bonds longer than 6 are present, and no CH2CH3 radicals are present;
• iv) CnF2n+1CFHCFHCmF2m+1 where n equals 1 to 4;
• and m equals 1 to 4;
• v) CF3CH2CF2CH3;
• vi) F[CF(CF3)CF2O]nCFHCF3 where n 1 to 5;
• vii) F[CF(CF3)CF2O]nCF2CF3 where n=1 to 5;
• viii) HCF2(OCF2)n(OCF2CF2)mOCF2H where n+m=1 to 8;
• ix) cyclic, linear, or branched hydrofluorocarbon amines and ether-amines in which there are more fluorines than hydrogens, no runs of hydrogen longer than two (CH—CH), no —CH2CH3 radicals are present and no runs of adjacent C—F bonds longer than 6 (CF—CF—CF—CF—CF—CF), and no C—H bonds immediately adjacent to either nitrogen or oxygen;
• and,
• x) XRfa(ORfb)w(ORfc)x(ORfd)yORfeY
• where X═H or F;
• Rfa and Rfe are independently a linear or branched fluoroalkyl radical of 1 to 3 carbons;
• Rfb, Rfc, and Rfd are linear or branched fluoroalkenyl radicals of 1-3 carbons;
• and w, x, and y=0 to 10 with the proviso that w+x+y>2;
• at least until the desired concentration of said one or more photochemically active species is achieved.

A process for forming an optical image on a substrate, the process comprising:

• a) radiating electromagnetic radiation from source capable of radiating electromagnetic radiation in the range of 140-260 nm;
• b) receiving said radiation on a target disposed to receive at least a portion of said radiation;
• and
• causing at least a portion of said radiation to traverse one or more optically transparent compositions disposed between said radiation source and said target, at least one of said optically transparent compositions comprising a composition comprising less than 20 parts per million of water, less than 90 parts per million of oxygen, and one or more compounds selected from the group consisting of:
• i) cyclic, linear, or branched hydrofluorocarbons having 2 to 10 carbon atoms in which there are more fluorines than hydrogen, no runs of adjacent C—H bonds longer than two (CH—CH), no runs of adjacent C—F bonds longer than 6 (CF—CF—CF—CF—CF—CF), and no —CH2CH3 radicals;
• ii) X—Rfa[ORfb]nORfcY wherein X and Y can be hydrogen or fluorine and Rfa, Rfb, and Rfc are 1 to 3 carbon fluorocarbon radicals, linear or branched
• in which there are more fluorines than hydrogens, no runs of adjacent C—H bonds longer than two are present, no —CH2CH3 radicals are present and no sequences with hydrogen on both sides of an ether oxygen (CH—O—CH) are present;
• iii) CnF2n−v+2Hv wherein n=2 to 10, v<n+1, no runs of adjacent C—H bonds longer than two are present, no runs of adjacent C—F bonds longer than 6 are present, and no CH2CH3 radicals are present;
• iv) CnF2n+1CFHCFHCmF2m+1 where n equals 1 to 4;
• and m equals 1 to 4;
• v) CF3CH2CF2CH3;
• vi) F[CF(CF3)CF2O]nCFHCF3 where n=1 to 5;
• vii) F[CF(CF3)CF2O]nCF2CF3 where n=1 to 5;
• viii) HCF2(OCF2)n(OCF2CF2)mOCF2H where n+m=1 to 8;
• ix) cyclic, linear, or branched hydrofluorocarbon amines and ether-amines in which there are more fluorines than hydrogens, no runs of hydrogen longer than two (CH—CH), no —CH2CH3 radicals are present and no runs of adjacent C—F bonds longer than 6 (CF—CF—CF—CF—CF—CF), and no C—H bonds immediately adjacent to either nitrogen or oxygen;
• and,
• x) XRfa(ORfb)w(ORfc)x(ORfd)yORfeY
• where X═H or F;
• Rfa and Rfe are independently a linear or branched fluoroalkyl radical of 1 to 3 carbons;
• Rfb, Rfc, and Rfd are linear or branched fluoroalkenyl radicals of 1-3 carbons;
• and w, x, and y=0 to 10 with the proviso that w+x+y>2.

A process for forming an optical image on a substrate, the process comprising:

• radiating electromagnetic radiation from a source capable of radiating electromagnetic radiation in the range of 140-260 nm;
• receiving said radiation on a target disposed to receive at least a portion of said radiation;
• and
• wherein one or more optically transparent compositions is disposed between said radiation source and said target, at least one of said optically transparent compositions comprising a composition treated with one or more means for extracting one or more photochemically active species, the composition comprising one or more compounds selected from the group consisting of:
• i) cyclic, linear, or branched hydrofluorocarbons having 2 to 10 carbon atoms in which there are more fluorines than hydrogen, no runs of adjacent C—H bonds longer than two (CH—CH), no runs of adjacent C—F bonds longer than 6 (CF—CF—CF—CF—CF—CF), and no —CH2CH3 radicals;
• i) X—Rfa[ORfb]nORfcY wherein X and Y can be hydrogen or fluorine and Rfa, Rfb, and Rfc are 1 to 3 carbon fluorocarbon radicals, linear or branched
• in which there are more fluorines than hydrogens, no runs of adjacent C—H bonds longer than two are present, no —CH2CH3 radicals are present and no sequences with hydrogen on both sides of an ether oxygen (CH—O—CH) are present;
• iii) CnF2n−y+2Hv wherein n=2 to 10, v<n+1, no runs of adjacent C—H bonds longer than two are present, no runs of adjacent C—F bonds longer than 6 are present, and no CH2CH3 radicals are present;
• iv) CnF2n+1CFHCFHCmF2m+1 where n equals 1 to 4;
• and m equals 1 to 4;
• v) CF3CH2CF2CH3;
• vi) F[CF(CF3)CF2O]nCFHCF3 where n=1 to 5;
• vii) F[CF(CF3)CF2O]nCF2CF3 where n=1 to 5;
• viii) HCF2(OCF2)n(OCF2CF2)mOCF2H where n+m=1 to 8;
• ix) cyclic, linear, or branched hydrofluorocarbon amines and ether-amines in which there are more fluorines than hydrogens, no runs of hydrogen longer than two (CH—CH), no —CH2CH3 radicals are present and no runs of adjacent C—F bonds longer than 6 (CF—CF—CF—CF—CF—CF), and no C—H bonds immediately adjacent to either nitrogen or oxygen;
• and,
• x) XRfa(ORfb)w(ORfc)x(ORfd)yORfeY
• where X═H or F;
• Rfa and Rfe are independently a linear or branched fluoroalkyl radical of 1 to 3 carbons;
• Rfb, Rfc, and Rfd are linear or branched fluoroalkenyl radicals of 1-3 carbons;
• and w, x, and y=0 to 10 with the proviso that w+x+y>2.

A process for forming an optical image on a substrate, the process comprising:

• radiating electromagnetic radiation from a source capable of radiating electromagnetic radiation in the range of 140-260 nm;
• receiving said radiation on a target disposed to receive at least a portion of said radiation;
• and
• wherein at least one of said target or said source is immersed in one or more optically transparent fluorinated organic liquids characterized by an absorbance per centimeter of <5 disposed between said radiation source and said target, at least one of said optically transparent fluorinated organic compounds having been subject to treatment with one or more means for extracting one or more photochemically active species.