Photosensitive resin composition and cured film prepared therefrom
Disclosed herein are a photosensitive resin composition and a cured film prepared therefrom. The photosensitive resin composition introduces a siloxane polymer containing a fluorine atom which has strong water-repellency into a composition including a common siloxane polymer and an epoxy compound, and fluorine groups may be present in the whole region of the cured film so that the water-repellency due to a fluorine component may be maintained even after removing the surface of the cured film is removed via a dry etching process. As a result, the resistance (chemical resistance) to chemicals used in a post-processing can be maximizes to provide a cured film having excellent stability.
1. A photosensitive resin composition, comprising:
(A) a siloxane polymer containing a fluorine atom;
(B) a 1,2-quinonediazide compound; and
(C) an epoxy compound,
wherein the siloxane polymer containing a fluorine atom(A) comprises at least one structural unit derived from a silane compound represented by the following formula 1:
(R 1 ) n Si(OR 2 ) 4-n [Formula 1]
in formula 1, R 1 is a fluorine atom or a monovalent hydrocarbon containing a fluorine atom, wherein, in case where R 1 is the monovalent hydrocarbon, hydrogen atoms may be partially or wholly substituted, and in case where a plurality of R 1 is present in the same molecule, each R 1 may be identical to or different from one another;
R 2 is hydrogen, alkyl having 1 to 6 carbon atoms, acyl having 2 to 6 carbon atoms, or aryl having 6 to 15 carbon atoms, wherein, in case where a plurality of R 2 is present in the same molecule, each R 2 may be identical to or different from one another, and in case where R 2 is alkyl, acyl or aryl, hydrogen atoms may be partially or wholly substituted; and
n is an integer from 1 to 3,
wherein the siloxane polymer (A) containing a fluorine atom is included in an amount of 50 to 95 wt % based on the total weight of the solid content of the composition excluding solvents, and
wherein the epoxy compound (C) is included in the photosensitive resin composition in an amount of 5 to 25 parts by weight based on 100 parts by weight of the siloxane polymer (A) on the basis of the solid content excluding solvents.
2. The photosensitive resin composition of claim 1 , wherein the epoxy compound(C) does not include a carboxyl group.
3. The photosensitive resin composition of claim 1 , wherein the siloxane polymer containing a fluorine atom(A) further comprises at least one structural unit derived from a silane compound represented by the following formula 2:
(R 3 ) n Si(OR 2 ) 4-n [Formula 1]
in formula 2, R 3 is alkyl having 1 to 12 carbon atoms, alkenyl having 2 to 10 carbon atoms or aryl having 6 to 15 carbon atoms, wherein, in case where a plurality of R 3 is present in the same molecule, each R 3 may be identical to or different from one another, in case where R 3 is alkyl, alkenyl or aryl, hydrogen atoms may be partially or wholly substituted, and R 3 may include a structural unit containing a heteroatom;
R 4 is hydrogen, alkyl having 1 to 6 carbon atoms, acyl having 2 to 6 carbon atoms, or aryl having 6 to 15 carbon atoms, wherein, in case where a plurality of R 4 is present in the same molecule, each R 4 may be identical to or different from one another, and in case where R 4 is alkyl, acyl or aryl, hydrogen atoms may be partially or wholly substituted; and
n is an integer from 0 to 3.
4. The photosensitive resin composition of claim 3 , wherein the siloxane polymer containing a fluorine atom(A) comprises a structural unit derived from a silane compound of formula 2 where n is 0.
5. The photosensitive resin composition of claim 1 , wherein the siloxane polymer containing a fluorine atom(A) comprises the fluorine atom in an amount of 1 to 30% of the content(mole %) of the fluorine-containing structural unit in the siloxane polymer based on an Si atomic mole number.
6. A method of forming a pattern, comprising:
forming a silicon-containing film on a surface of a substrate using a photosensitive resin composition, comprising (A) a siloxane polymer containing a fluorine atom, (B) a 1,2-quinonediazide compound and (C) an epoxy compound;
patterning the silicon-containing film using light; and
dry etching the patterned silicon-containing film and the substrate to form a pattern in the substrate,
wherein the siloxane polymer containing a fluorine atom(A) comprises at least one structural unit derived from a silane compound represented by the following formula 1:
(R 1 ) n Si(OR 2 ) 4-n [Formula 1]
in formula 1, R 1 is a fluorine atom or a monovalent hydrocarbon containing a fluorine atom, wherein, in case where R 1 is the monovalent hydrocarbon, hydrogen atoms may be partially or wholly substituted, and in case where a plurality of R 1 is present in the same molecule, each R 1 may be identical to or different from one another;
R 2 is hydrogen, alkyl having 1 to 6 carbon atoms, acyl having 2 to 6 carbon atoms, or aryl having 6 to 15 carbon atoms, wherein, in case where a plurality of R 2 is present in the same molecule, each R 2 may be identical to or different from one another, and in case where R 2 is alkyl, acyl or aryl, hydrogen atoms may be partially or wholly substituted; and
n is an integer from 1 to 3,
wherein the siloxane polymer (A) containing a fluorine atom is included in an amount of 50 to 95 wt % based on the total weight of the solid content of the composition excluding solvents, and
wherein the epoxy compound (C) is included in the photosensitive resin composition in an amount of 5 to 25 parts by weight based on 100 parts by weight of the siloxane polymer (A) on the basis of the solid content excluding solvents.
7. A silicon-containing cured film formed by a method of forming a pattern, comprising:
forming a silicon-containing film on a surface of a substrate using a photosensitive resin composition, comprising (A) a siloxane polymer containing a fluorine atom, (B) a 1,2-quinonediazide compound and (C) an epoxy compound;
patterning the silicon-containing film using light; and
dry etching the patterned silicon-containing film and the substrate to form a pattern in the substrate,
wherein the siloxane polymer containing a fluorine atom(A) comprises at least one structural unit derived from a silane compound represented by the following formula 1:
(R 1 ) n Si(OR 2 ) 4-n [Formula 1]
in formula 1, R 1 is a fluorine atom or a monovalent hydrocarbon containing a fluorine atom, wherein, in case where R 1 is the monovalent hydrocarbon, hydrogen atoms may be partially or wholly substituted, and in case where a plurality of R 1 is present in the same molecule, each R 1 may be identical to or different from one another;
R 2 is hydrogen, alkyl having 1 to 6 carbon atoms, acyl having 2 to 6 carbon atoms, or aryl having 6 to 15 carbon atoms, wherein, in case where a plurality of R 2 is present in the same molecule, each R 2 may be identical to or different from one another, and in case where R 2 is alkyl, acyl or aryl, hydrogen atoms may be partially or wholly substituted; and
n is an integer from 1 to 3,
wherein the siloxane polymer (A) containing a fluorine atom is included in an amount of 50 to 95 wt % based on the total weight of the solid content of the composition excluding solvents, and
wherein the epoxy compound (C) is included in the photosensitive resin composition in an amount of 5 to 25 parts by weight based on 100 parts by weight of the siloxane polymer (A) on the basis of the solid content excluding solvents.
8. The silicon-containing cured film of claim 7 , wherein the silicon-containing cured film has a contact angle of 80° or more after dry etching.