Process for preparing fluorine-containing norbornene derivative
AssigneeDaikin Industries, Ltd.
InventorsTakayuki Araki, Takuji Ishikawa, Takuji Kume, Akinori Yamamoto
Life of this patent
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Abstract
There are provided a novel norbornene derivative which is a material for a chemically amplifying type photoresist for F2 laser, possesses excellent transparency and improved dry etching resistivity and has a fluorine-containing ketone unit or fluorine-containing tertiary alcohol unit directly bonded to the norbornene backbone; a fluorine-containing polymer obtained by using the norbornene derivative as a copolymerizable monomer; and a chemically amplifying type photoresist composition comprising the fluorine-containing polymer, a photoacid generator and a solvent.
Claims26
A process for preparing a fluorine-containing norbornene derivative having a fluorine-containing tertiary alcohol structure which is represented by the formula (4):
- wherein Z1 is the same or different and each is:
- R1)n2-Z2
- in which Z2 is:
- wherein Rf1 is a fluorine-containing alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and ether bond, Rf2 is a fluorine-containing alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and ether bond, R3 is H or a hydrocarbon group having 1 to 10 carbon atoms, R1 is a divalent organic group, n2 is 0 or 1;
- Y is the same or different and each is H, F, Cl, an alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and may have ether bond;
- R is the same or different and each is H or an alkyl group having 1 to 10 carbon atoms;
- n is 0 or an integer of from 1 to 5;
- m is an integer of from 1 to 5;
- n1 is an integer of from 1 to 5;
- m+n1=6, said process being characterized by reacting a norbornene derivative represented by the formula (3):
- wherein X3 is the same or different and each is:
- R1)n2—X4
- in which X4 is —COOR2,
- wherein R2 is an alkyl group having 1 to 5 carbon atoms, X5 is halogen atom;
- R3, Rf1, R1, Y, R, m, n, n1 and n2 are as defined above, with a fluoroalkylation agent which introduces Rf2 to X4.
A norbornene derivative having a fluorine-containing alcohol structure represented by the formula (8):
- wherein Z4 is the same or different and each is:
- in which Rf4 is the same or different and each is a fluorine-containing alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and ether bond, R3 is H or a hydrocarbon group having 1 to 10 carbon atoms;
- Y is the same or different and each is H, F, Cl, an alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and may have ether bond;
- R is the same or different and each is H or an alkyl group having 1 to 10 carbon atoms;
- n is 0 or an integer of from 1 to 5;
- m is an integer of from 1 to 5;
- n1 is an integer of from 1 to 5;
- m+n1=6.
A norbornene derivative having a fluorine-containing alcohol structure represented by the formula (9):
- wherein Z5 is the same or different and each is:
- in which Rf4 and Rf5 are the same or different and each is a fluorine-containing alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and ether bond;
- Y is the same or different and each is H, F, Cl, an alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and may have ether bond;
- R is the same or different and each is H or an alkyl group having 1 to 10 carbon atoms;
- n is 0 or an integer of from 1 to 5;
- m is an integer of from 1 to 5;
- n1 is an integer of from 1 to 5;
- m+n1=6.
A norbornene derivative having a fluorine-containing alcohol structure represented by the formula (10):
- wherein Rf4 and Rf5 are the same or different and each is a fluorine-containing alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and ether bond;
- Y is the same or different and each is H, F, Cl, an alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and may have ether bond;
- R is the same or different and each is H or an alkyl group having 1 to 10 carbon atoms;
- n is 0 or an integer of from 1 to 5.
A norbornene derivative having a fluorine-containing alcohol structure represented by the formula (11):
- wherein Rf4 and Rf5 are the same or different and each is a fluorine-containing alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and ether bond;
- Y is the same or different and each is H, F, Cl, an alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and may have ether bond;
- R is the same or different and each is H or an alkyl group having 1 to 10 carbon atoms;
- n is 0 or an integer of from 1 to 5.
A norbornene derivative having a fluorine-containing alcohol structure represented by the formula (12):
- wherein Rf4 and Rf5 are the same or different and each is a fluorine-containing alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and ether bond;
- Y1, Y2 and Y3 are the same or different and each is H, F, Cl, an alkyl group having 1 to 10 carbon atoms or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and may have ether bond;
- R is the same or different and each is H or an alkyl group having 1 to 10 carbon atoms;
- n is 0 or an integer of from 1 to 5;
- at least one of Y1, Y2 and Y3 is F or a fluorine-containing alkyl group which has 1 to 10 carbon atoms and may have ether bond.
Dependencies are inferred from the claim text.