(Meth)acrylate, raw material alcohol for the (meth)acrylate, method of producing the (meth)acrylate and the alcohol, polymer produced by polymerizing the (meth)acrylate, chemically amplified resist composition, and method of the formation of a pattern
View Patent ↗A (meth)acrylate represented by the following formula (1): wherein each of R 1 , R 2 , R 3 and R 4 represents a hydrogen atom, a methyl group or an ethyl group; either one of X 1 or X 2 represents a (meth)acryloyloxy group and the other represents a hydrogen atom; both A 1 and A 2 represent hydrogen atoms, or A 1 and A 2 form —O—, —CH 2 — or —CH 2 CH 2 —, which can be produced by first producing a lactone by reducing an addition product obtained by the Diels-Alder reaction between 1,3-diene and maleic anhydride, and then hydrating the lactone to produce an alcohol followed by (meth)acrylation of the alcohol; a polymer produced by (co)polymerizing a monomer composition comprising the (meth)acrylate of the present invention is excellent in transparency, dry etching resistance, and solubility in organic solvents, and so it is preferably used as a resin for a chemically amplified resist composition.
1. A polymer produced by (co)polymerizing a monomer composition comprising the monomer represented by formula (1):
wherein each of R 1 , R 2 , R 3 and R 4 represents a hydrogen atom, a methyl group or an ethyl group; either one of X 1 or X 2 represents a (meth)acryloyloxy group and the other represents a hydrogen atom; both A 1 and A 2 represent hydrogen atoms, or A 1 and A 2 form —O—, —CH 2 — or —CH 2 CH 2 —.
2. The polymer according to claim 1 , wherein, any one of R 1 , R 2 , R 3 and R 4 represents a methyl group and the others represent hydrogen atoms.
3. The polymer according to claim 1 , which is represented by the following formula (5-1):
wherein each of R 1 , R 2 , R 3 and R 4 represents a hydrogen atom, a methyl group or an ethyl group; each of R 5 , R 7 and R 9 represents a hydrogen atom or a methyl group; R 6 represents a cyclic hydrocarbon group having a group that is eliminated by acid; R 8 represents a group having a hydrophilic functional group or a hydrogen atom; both A 1 and A 2 represent hydrogen atoms, or A 1 and A 2 form —O—, —CH 2 — or —CH 2 CH 2 —; and x 2 , y 2 and z 2 represent the ratios of a unit (A), a unit (B) and a unit (C), respectively, wherein, when x 2 +y 2 +z 2 =1, x 2 , y 2 and z 2 are any given numbers satisfying 0<x 2 ≦1, 0≦y 2 <1, and 0≦z 2 <1.
4. The polymer according to claim 3 , wherein R 6 contains at least one selected from the group consisting of a cyclohexyl group, an isobornyl group, an adamantyl group, a tricyclodecanyl group, a dicyclopentadienyl group, and substituted compounds thereof.
5. The polymer according to claim 1 , which is represented by the following formula (5-2):
wherein each of R 1 , R 2 , R 3 and R 4 represents a hydrogen atom, a methyl group or an ethyl group; each of R 5 and R 7 represents a hydrogen atom or a methyl group; R 6 represents a cyclic hydrocarbon group having a group that is eliminated by acid; both A 1 and A 2 represent hydrogen atoms, or A 1 and A 2 form —O—, —CH 2 — or —CH 2 CH 2 —; and x 3 , y 3 and z 3 represent the ratios of a unit (A), a unit (B) and a unit (D), respectively, wherein, when x 3 +y 3 +z 3 =1, x 3 , y 3 and z 3 are any given numbers satisfying 0<x 3 ≦1, 0≦y 3 <1, and 0≦z 3 <1.
6. The polymer according to claim 5 , wherein R 6 contains at least one selected from the group consisting of a cyclohexyl group, an isobornyl group, an adamantyl group, a tricyclodecanyl group, a dicyclopentadienyl group, and substituted compounds thereof.
7. The polymer according to claim 1 , which is represented by the following formula (5-3):
wherein each of R 1 , R 2 , R 3 , R 4 , R 10 and R 11 represents a hydrogen atom, a methyl group or an ethyl group; each of R 5 and R 7 represents a hydrogen atom or a methyl group; R 6 represents a cyclic hydrocarbon group having a group that is eliminated by acid; both A 1 and A 2 represent hydrogen atoms, or A 1 and A 2 form —O—, —CH 2 — or —CH 2 CH 2 —; n represents an integer of 0 to 4; and x 4 , y 4 and z 4 represent the ratios of a unit (A), a unit (B) and a unit (E), respectively, wherein, when x 4 +y 4 +z 4 =1, x 4 , y 4 and z 4 are any given numbers satisfying 0<x 4 ≦1, 0≦y 4 <1, and 0≦z 4 <1.
8. The polymer according to claim 7 , wherein R 6 contains at least one selected from the group consisting of a cyclohexyl group, an isobornyl group, an adamantyl group, a tricyclodecanyl group, a dicyclopentadienyl group, and substituted compounds thereof.
9. The polymer according to claim 1 , which has a weight-average molecular weight of 1,000 to 100,000.
10. The polymer according to claim 3 , which has a weight-average molecular weight of 1,000 to 100,000.
11. The polymer according to claim 5 , which has a weight-average molecular weight of 1,000 to 100,000.
12. The polymer according to claim 7 , which has a weight-average molecular weight of 1,000 to 100,000.
13. The polymer according to claim 1 wherein A 1 and A 2 form —CH 2 —.