Deep UV sensitive resistant to latent image decay comprising a diazonaphthoquinone sulfonate of a nitrobenzyl derivative

• US 5,314,782 A
• Filed: 03/05/1993
• Issued: 05/24/1994
• Est. Priority Date: 03/05/1993
• Status: Expired due to Fees

• Current Assignee: Morton International Incorporated (Autoliv Incorporated)
• Original Assignee: Morton International Incorporated (Autoliv Incorporated)
• Inventors: Lazarus, Richard M., Koes, Thomas A.
• Primary Examiner(s): Bowers, Jr., Charles L.
• Assistant Examiner(s): CHU, JOHN S Y
• Application Number:
  US08/026,934
• Time in Patent Office: 445 Days
• Field of Search: 430/190, 430/191, 430/192, 430/193, 430/165, 430/270, 430/271, 534/556, 534/557
• US Class Current: 430/165
• CPC Class Codes: G03F 7/0045 with organic non-macromolecular light-sensitive compounds not otherwise provided for, e.g. dissolution inhibitors
• CPC Class Codes: G03F 7/022 Quinonediazides G03F7/075 takes precedence

Abstract

A positive working deep UV sensitive photoresist which provides improved critical dimension stability during prolonged periods of post exposure delay before baking comprises an acid stable polymer which is insoluble in water but normally soluble in an aqueous alkaline medium, a photo acid generator exemplified by the tri-(2,1,4-diazonaphthoquinonesulfonate) ester of 3,5-dinitro-2,6-dimethylol para cresol, and a mixed carbonate ester of tertiary butyl alcohol and a polyhydric phenol which is an acid labile compound which inhibits the dissolution of the normally soluble polymer in said alkaline medium.

Claims

1. A positive working photoresist composition comprising, in admixture:

a polymer insoluble in water but normally soluble in an aqueous alkaline medium;

a photo acid generator having the formula;

##STR4## wherein Q is a diazonaphthoquinone moiety;

R is hydrogen or the --CH_2- OS(═

O)₂ --Q moiety;

R¹ is hydrogen, hydroxyl, or --O--S(═

O)₂ --Q;

R² is hydrogen or lower alkyl; and

X is hydrogen or a nitro group, with the proviso that R² is lower alkyl when X is a nitro group; and

a mixed carbonate ester of tertiary butyl alcohol and a polyhydric phenol which is a discrete acid labile inhibitor of the dissolution of the polymer insoluble in water but normally soluble in aqueous alkaline medium.

2. The composition of claim 1, wherein R, R¹, R², and X are hydrogen.

3. The composition of claim 1 wherein R¹ is --O--S(═

O)₂ --Q;

R² is lower alkyl; and

X is nitro group.

4. The composition of claim 1 wherein the photo acid generator is the tri-(2,1,4-diazonaphthoquinonesulfonate) ester of 3,5-dinitro-2,6-dimethylol para cresol.

5. The composition of claim 1 further comprising a 1-naphthalene sulfonic acid, 3-diazo-3,4-dihydro-4-oxo ester of a cresol/formaldehyde polymer.

6. The composition of claim 1 wherein the polyhydric phenol is pyrogallol.

7. The composition of claim 1 wherein the polyhydric phenol is a product of the condensation of acetone and pyrogallol.

8. The composition of claim 7 wherein the polyhydric phenol is hexahydroxyspirobiindene.

13. The composition of claim 1 wherein the carbonate ester is from about 3% to about 5% by weight of the total weight.

14. The composition of claim 5 wherein the amount of the oxo ester is from about 3% to about 5% by weight of the total.

21. The composition of claim 1 wherein the polyhydric phenol is selected from the group consisting of pyrogallol, resorcinol, catechol, hydroquinone, phloroglucinol, hydroxyhydroquinone, trihydroxybenzophenone, and tetrahydroxybenzophenone.

9. A radiation sensitive composition comprising, in admixture:

a photo acid generator having the formula;

##STR5## wherein Q is a diazonaphthoquinone moiety;

R is hydrogen or the --CH_2- OS(═

O)₂ --Q moiety;

R¹ is hydrogen, hydroxyl, or --O--S(═

O)₂ --Q;

R² is hydrogen or lower alkyl;

X is hydrogen or a nitro group, with the proviso that R² is lower alkyl when X is a nitro group; and

an acid labile carbonate ester of tertiary butyl alcohol and a polyhydric phenol.

10. The composition of claim 9 wherein the polyhydric phenol is pyrogallol.

11. The composition of claim 9 wherein R is the --CH_2- OS(═

O)₂ --Q moiety.

12. The composition of claim 9 wherein R¹ is --O--S(═

O)₂ --Q;

R² is lower alkyl; and

X is a nitro group.

15. A radiation sensitive recording material which comprises a support and a recording layer thereon, said recording layer comprising, in admixture:

an acid stable polymer insoluble in water but normally soluble in an aqueous alkaline medium;

a photo acid generator having the formula;

##STR6## wherein Q is a diazonaphthoquinone moiety;

R is hydrogen or the --CH_2- OS(═

O)₂ --Q moiety;

R¹ is hydrogen, hydroxyl, or --O--S(═

O)₂ --Q;

R² is hydrogen or lower alkyl;

X is hydrogen or a nitro group, with the proviso that R² is lower alkyl when X is a nitro group; and

a mixed carbonate ester of tertiary butyl alcohol and a polyhydric phenol.

16. The recording material of claim 15 wherein the polyhydric phenol is pyrogallol.

17. The recording material of claim 15 wherein the polyhydric phenol is a condensation product of acetone and pyrogallol.

18. The recording material of claim 15 wherein R is the --CH_2- OS(═

O)₂ --Q moiety.

19. The recording material of claim 15 wherein R¹ is --O--S(═

O)₂ --Q;

R² is lower alkyl; and

X is a nitro group.

20. The recording material of claim 15 wherein the photo acid generator is the tri-(2,1,4-diazonaphthoquinonesulfonate) ester of 3,5-dinitro-2,6-dimethylol para cresol.