Photoresist compositions

1. A photoresist composition oomprising a polymer mixture comprising a copolymer (A) containing a α-gamma-butyrolactone methacrylate monomer unit and a copolymner (B) containing a β-gamma-butyrolactone methacrylate monomer unit wherein copolymner (A) comprises the monomer units α-gamma-butyrolactone methacrylate, 2-methyl-2-adamantyl methacrylate, and 2-cyano-5-norbornyl methacrylate.

2. The photoresist composition of claim 1 wherein copolymer (B) comprises the monomer units β-gamma-butyrolactone methacrylate, 2-methyl-2-adamantyl methacrylate, and 2-cyano-5-norbomyl methacrylate.

3. A process for imaging a photoresist comprising the steps of:

a) coating a substrate with the photoresist composition of claim 1 ;

b) baking the substrate to substantially remove the solvent;

c) image-wise exposing the photoresist coating;

d) post-exposure baking the photoresist coating; and

e) developing the photoresist coating with an aqueous alkaline solution.

4. The process according to claim 3 wherein copolymer (B) comprises the monomer units β-gamma-butyrolactone methacrylate, 2-methyl-2-adamantyl methacrylate, and 2-cyano-5-norbornyl methacrylate.

5. A method for producing a microelectronic device by forming an image on a substrate comprising:

a) providing a photoresist composition of claim 1 ;

b) coating a suitable substrate with the photoresist composition of step a); and

c) heat treating the coated substrate of step b) until substantially all of the phtotoresist solvent is removed; image-wise exposing the photoresist composition and removing the image-wise exposed areas of such composition with a suitable developer.

6. A photoresist composition comprising a polymer mixture comprising a copolymer (A) containing a α-gamma-butyrolactone methacrylate monomer unit and a copolymer (B) containing a β-gamma-butyrolactone methacrylate monomer unit wherein the ratio of copolymers (A) and (B) is from about 90:10 weight percent to about 10:90 weight percent wherein copolymer (A) comprises the monomer units α-gamma-butyrolactone methacrylate, 2-methyl-2-adamantyl methacrylate, and 2-cyano-5-norbornyl methacrylate.

7. The photoresist composition of claim 6 wherein copolymer (B) comprises the monomer units β-gamma-butyrolactone methacrylate, 2-methyl-2-adamantyl methacrylate, and 2-cyano-5-norbornyl methacrylate.

8. A process for imaging a photoresist comprising the steps of:

a) a coating a substrate with the photoresist composition of claim 6 ;

b) baking the substrate to substantially remove the solvent;

c) image-wise exposing the photoresist coating;

d) post-exposure baking the photoresist coating; and

e) developing the photoresist coating with an aqueous alkaline solution.

9. The process according to claim 8 wherein copolymer (B) comprises the monomer units β-gamma-butyrolactone methacrylate, 2-methyl-2-adamantyl methacrylate, and 2-cyano-5-norbornyl methacrylate.

10. A method for producing a microelectronic device by forming an image on a substrate comprising:

a) providing a photoresist composition of claim 6 ;

b) coating a suitable substrate with the photoresist composition of step a); and

c) heat treating the coated substrate of step b) until substantially all of the photoresist solvent is removed; image-wise exposing the photoresist composition and removing the image-wise exposed areas of such composition with a suitable developer.

11. A photoresist composition comprising a polymer selected from the group consisting of poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-2-cyano-5-norbornyl methacrylate); poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-β-gamma-butyrolactone methacrylate-co-2-cyano-5-norbornyl methacrylate); poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-4-isopropy-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2bicyclo[2.2.2]octanecarbolactone); poly(2-ethyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-2-cyano-5-norbornyl methacrylate); poly(2-ethyl-2-adamantyl methacrylate-co-α-gammna-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-ethyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyolo[2.2.2]octanecarbolactone); poly(2-ethyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(2-ethyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-2-cyano-5-norbornyl methacrylate); poly(2-methyl-2-adamantyl methacrylate-co-3-hydroxy-1-methacryloxyadamantane-co-2-cyano-5-norbornyl methacrylate); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-2-cyano-5-norbornyl methacrylate-co-5-methacryloyloxy-2,6-norbornanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-5-methacryloyloxy-2,6-norbornanecarbolactone-co-2-cyano-5-norbornyl methacrylate); poly(2-methyl-2-adamantyl methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-3-hydroxy-1-methacryloxyadamantane-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2 2.2]octanecarbolactone); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy -2,6-bicyclo[2.2.2]octanecarbolactone-co-5methacryloyloxy-2,6-norbornanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-5-methacryloyloxy-2,6-norbornanecarbolactone-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyolo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-3-hydroxy-1-methacryloxyadamantane-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone-co-5-methacryloyloxy-2,6-norbornanecarbolactone); poly(α-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-2-cyano-5-norbornyl methacrylate); poly(α-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-2-cyano-5-norbornyl methacrylate); poly(β-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-2-cyano-5-norbornyl methacrylate); poly(α-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(β-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(α-gamma-butyrolactone methacrylate-co-2-ethyl-2adamantyl methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(β-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(α-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(β-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(α-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(β-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); and poly(2-methyl-2-adamantyl methacrylate-co-5-methacryloyloxy-2,6-norbornanecarbolactone-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone).

12. The photoresist composition of claim 11 wherein the polymer is selected from the group consisting of poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-β-gamma-butyrolactone methacrylate-co-2-cyano-5-norbornyl methacrylate); poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2 2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolaotone); poly(2-ethyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-2-cyano-5-norbornyl methacrylate); poly(2-ethyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-ethyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bioyclo[2.2.2]octanecarbolactone); poly(2-ethyl-2-adamantyl methacrylate-co-α-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bioyclo[2.2.2]octanecarbolactone); poly(2-ethyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-2-cyano-5-norbornyl methacrylate); poly(2-methyl-2-adamantyl methacrylate-co-3-hydroxy-1-methacryloxyadamantane-co-2-cyano-5-norbornyl methacrylate); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-2-cyano-5-norbornyl methacrylate-co-5-methacryloyloxy-2,6-norbornanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-5-methacryloyloxy-2,6-norbornanecarbolactone-co-2-cyano-5-norbornyl methacrylate); poly(2-methyl-2-adamantyl methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2adamantyl methacrylate-co-3-hydroxy-1-methacryloxyadamantane-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6bicyclo[2.2.2]octanecarbolactone); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone-co-5-methacryloytoxy-2,6-norbornanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-5-methacryloyloxy-2,6-norbornanecarbolactone-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(2-methyl-2-adamantyl methacrylate-co-3-hydroxy-1-methacryloxyadamantane-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-β-gamma-butyrolactone methacrylate-co-4isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(t-butyl norbornene carboxylate-co-maleic anhydride-co-2-methyl-2-adamantyl methacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone-co-5-methacryloyloxy-2,6-norbornanecarbolactone); poly(α-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyolopentylmethacrylate-co-2-cyano-5-norbornyl methacrylate); poly(β-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-2-cyano-5-norbornyl methacrylate); poly(β-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-2-cyano-5-norbornyl methacrylate); poly(α-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(β-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(α-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1methyl-5methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(β-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cycopentylmethacrylate-co-4-isopropyl-1-methyl-5-methacryloyloxy-2,6-bicyclo[2.2.2]octanecarbolactone); poly(α-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(β-gamma-butyrolactone methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(α-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cyclopentylmethacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); poly(β-gamma-butyrolactone methacrylate-co-2-ethyl-2-adamantyl methacrylate-co-1-ethyl-1-cyolopentylmethacrylate-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bicyclo[2.2.2]octanecarbolactone); and poly(2-methyl-2-adamantyl methacrylate-co-5-methacryloyloxy-2,6-norbornanecarbolactone-co-4-isopropyl-1-methyl-5-methoxy-6-methacryloyloxy-3,2-bioyclo[2.2.2]octanecarbolactone).