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US 2006/0217519 A1Published application
Photoresist polymers
AssigneeJsr Corporation
InventorsDidier Benoit, Adam Safir, Han-Ting Chang, Dominique Charmot, Kenji Okamoto, Isao Nishimura, Yong Wang
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Abstract
The present invention is directed to the preparation of photoresist polymers via living free radical polymerization techniques. Sterically bulky ester monomers are utilized as the polymerization components. Use of chain transfer agents is included in polymerization processing conditions. Cleavage of polymer terminal end groups that include a heteroatom are described.
Claims28
A polymer comprising the formula:
- [A]x[B]y[C]z
- wherein A, B and C are each individually one of
- wherein x is between about 0 and about 200 inclusive, y is between about 1 and about 200 inclusive and z is between about 1 and about 200 inclusive, provided B≠C
- wherein the polymer is prepared by a living free radical process (LFRP) in the presence of a chain transfer agent (CTA) having the formula:
- wherein R1 is any group that can be expelled as its free radical form in an addition-fragmentation reaction;
- R2 and R3 are each independently selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl, and combinations thereof, and optionally R2 and R3 together to form a double bond optionally substituted alkenyl moiety;
- R4 is selected from the group consisting of hydrogen, hydrocarbyl, substituted hydrocarbyl, heteroatom-containing hydrocarbyl, and substituted heteroatom-containing hydrocarbyl, and combinations thereof;
- and optionally, R4 combines with R2 and/or R3 to form a ring structure, with said ring having from 3 to 50 non-hydrogen atoms;
- and
- D is either sulfur, selenium or tellurium.
7 more elements
A polymer comprising at least one recurring unit having the formula:
- wherein R1 represents a hydrogen atom, trifluoromethyl or a methyl group, each R2, individually, represents a linear or branched, non-substituted or substituted, alkyl group having 1-4 carbon atoms or a bridged or non-bridged, non-substituted or substituted, monovalent alicyclic hydrocarbon group having 4-20 carbon atoms, provided that at least one R2 group is a linear or branched alkyl group having 1-4 carbon atoms, or any two R2 groups form, in combination and together with the carbon atoms to which the two R2 groups bond, a bridged or non-bridged, non-substituted or substituted, divalent alicyclic hydrocarbon group having 4-20 carbon atoms, with the remaining R2 groups being a linear or branched, non-substituted or substituted, alkyl group having 1-4 carbon atoms or —C(R2)3, is one of
- such that the
- indicates that the bond carbon bond is directly attached to the ester oxygen;
- and
- at least a second recurring unit selected from
- wherein R2 represents a hydrogen atom or a methyl group, R3 is a linear or branched alkyl group having 1-6 carbon atoms or a linear or branched alkyl group having 1-6 carbon atoms substituted with one or more alkyloxy, alkylcarbonyloxy or oxo groups, two or more R3 groups, if present, being either the same or different, i is an integer of 0−(3+k), j is 0 or 1, k is an integer of 1-3, R4 represents a hydrogen atom or a methyl group, B is a methylene group, an oxygen atom, or a sulfur atom, R5 represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms, or a linear or branched alkyl group having 1-6 carbon atoms substituted with one or more alkyloxy, alkylcarbonyloxy or oxo groups, R6 represents a hydrogen atom or a methyl group, and R7 represents a hydrogen atom, a linear or branched alkyl group having 1-6 carbon atoms;
- and
- wherein the polymer is prepared by a living free radical process (LFRP) in the presence of a chain transfer agent (CTA) having the formula
- wherein Rx is a group that is sufficiently labile to be expelled as its free radical form, T is carbon or phosphorus, and Z is any group that activates the C═S double bond towards a reversible free radical addition fragmentation reaction.
6 more elements
Dependencies are inferred from the claim text.