Antireflective coatings for photoresist compositions

Abstract

The present invention relates to a novel antireflective coating solution and a process for its use in photolithography. The antireflective coating solution comprises a novel polymer and an organic solvent or a mixture of organic solvents, where the novel polymer comprises a unit containing a dye that absorbs from about 180 nm to about 450 nm and a unit containing a crosslinking group.

Description

Claims

1. An antireflecting coating composition for use in photolithography, comprising

a) a polymer comprising at least one dye unit having the structure, ##STR1## where R.sub.1 -R.sub.4 is H, (C.sub.1 -C.sub.4) alkyl or (C.sub.1 -C.sub.4) alkoxy,

R.sub.5 is OH, NH.sub.2, OCH.sub.3 or OCH.sub.2 CH.sub.3,

R.sub.6 is H, (C.sub.1 -C.sub.4) alkyl or (C.sub.1 -C.sub.4) alkoxy,

R.sub.7 is H, (C.sub.1 -C.sub.4) alkyl, (C.sub.1 -C.sub.4) alkoxy, nitro, chloro, cyano, dicyanovinyl or SO.sub.2 CF.sub.3,

R.sub.8 is nitro, chloro, cyano, dicyanovinyl, SO.sub.2 CF.sub.3, SONH.sub.2, COOY, SO.sub.3 Y, where Y is H,

X is a conjugated moiety N.dbd.N, CZ.dbd.CZ, CZ.dbd.N, N.dbd.CZ, where Z is H, (C.sub.1 -C.sub.4) alkyl or (C.sub.1 -C.sub.4) alkoxy,

m=1-3, and n=1-4; and,

at least one unit capable of crosslinking the polymer having the structure ##STR2## where Y contains a crosslinking functionality and R.sub.1 to R.sub.3 are H, (C.sub.1 -C.sub.4) alkyl or (C.sub.1 -C.sub.4) alkoxy and,

b) a suitable organic solvent.

2. The antireflective composition according to claim 1, wherein the solvent comprises a mixture of organic solvents.

3. The antireflective composition according to claim 1, wherein the solvent is selected from a group consisting of propylene glycol monomethyl ether, propylene glycol monomethyl etheracetate, ethyl lactate, cyclopentanone, cyclohexanone, and gamma butyrolactone.

4. The antireflective composition according to claim 1, wherein the crosslinking group is selected from a group consisting of carbodiimide, isocyanate, blocked isocyanate, glycidyl methacrylate, alkylol acrylamide, alkylol methacrylamide and methyl acrylamidoglycolate.

5. The antireflective composition according to claim 1, wherein X in the dye unit is an azo group.

6. The antireflective composition of claim 1, wherein the dye unit ranges from about 5 to about 95 mole percent and the crosslinking unit ranges from about 1 to about 50 mole percent of the polymer.

7. The antireflective composition according to claim 1, wherein the polymer further comprises one or more vinyl monomers that are nonabsorbing and noncrosslinking.

8. The antireflective composition according to claim 7, wherein the vinyl monomer is selected from a group consisting of maleic anhydride, vinyl acrylates, vinyl phenolics, vinyl ethers, vinyl acrylamides, vinyl carboxylic acids, vinyl sulphonic acids and N-(3-Hydroxyphenylmethacrylamide).

9. The antireflective composition according to claim 1, further comprising a dye.

10. The antireflective composition according to claim 1, further comprising a crosslinking agent.

11. The antireflective composition according to claim 1, wherein the polymer has a weight average molecular weight in the range of about 2,500 to about 1,000,000.

12. The antireflective composition according to claim 1, wherein the metal ion level is less than 50 ppb each metal ion.

13. The process of forming an image on a substrate comprising the steps of:

a) coating the substrate with the antireflective coating composition of claim 1,

b) heating the antireflective coating,

c) a coating from a photoresist solution on the substrate,

d) heating the photoresist coating to substantially remove solvent from the coating,

e) imagewise exposing the photoresist coating,

f) developing an image using an aqueous alkaline developer,

g) optionally, heating the substrate prior to and after development,

h) dry etching the antireflective coating.

14. The process of claim 13, wherein the photoresist solution comprises a novolak resin, a photosensitive compound and a solvent.

15. The process of claim 13, wherein the photoresist solution comprises a substituted polyhydroxystyrene, a photoactive compound and a solvent.

16. The process of claim 13, wherein the photoresist solution comprises polyhydroxystyrene, a photoactive compound, a dissolution inhibitor and a solvent.

17. The process of claim 13, wherein the heating temperature for the antireflective coating ranges from about 70.degree. C. to about 250.degree. C.

18. The process of claim 13, wherein the developer is an aqueous solution of metal ion free alkaline hydroxide.