Selected o-quinonediazide sulfonic acid esters of phenolic compounds and their use in radiation-sensitive compositions
AssigneeOCG Microelectronic Materials, Inc.
InventorsAndrew J. Blakeney, Arturo N. Medina, Medhat A. Toukhy, Lawrence Ferreira, Sobhy Tadros
Life of this patent
Estimating the term…
Abstract
A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB): ##STR1## wherein the photosensitive compound is used in a positive photoresist composition and process for forming patterned image. Further the invention is drawn to a positive photoresist composition comprising an alkali-soluble resin and quinone diazide sulfonic acid triesters and diesters characterized by their HPLC peak areas.
Claims48
A photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenolic compound, said esters selected from the group consisting of formulae (IB) and (IIB):
- ##STR28## wherein R.sub.1, R.sub.2, R.sub.11, and R.sub.12 are each independently selected from the group consisting of hydrogen, OD, halogen, lower alkyl group having 1 to 4 carbon atoms, lower alkyl ether groups having 1 to 4 carbon atoms, and lower alkyl thioether groups having 1 to 4 carbon atoms;
- wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.13, and R.sub.14 are each independently selected from the group consisting of hydrogen, halogen, lower alkyl groups having 1 to 4 carbon atoms lower alkyl ether groups having 1 to 4 carbon atoms;
- and lower alkyl thioether groups having 1 to 4 carbon groups;
- wherein x and y are each independently selected from an integer from the group 0, 1, 2, 3, and 4;
- wherein Ra, Rb, Rc, and Rd are each independently selected from hydrogen and a lower alkyl group having 1 to 4 carbon atoms;
- wherein v and w are each independently selected from an integer from the group 0 and 1 and each sum of v and w on a fused ring is 1 or 2;
- and
- wherein A and B are each independently selected from the group consisting of oxygen, sulfur, and a methylene radical;
- and
- wherein each OD group is a hydroxyl or an o-quinonediazide sulfonic acid ester group wherein each D is selected from the group consisting of naphthoquinonediazide sulfonyl group or benzoquinonediazide sulfonyl group, provided that at least one --OD is an o-quinonediazide sulfonic acid ester group.
A radiation sensitive composition as a positive working photoresist, said composition comprising an admixture of an alkali soluble binder resin and a photosensitive compound comprising at least one o-quinonediazide sulfonic acid ester of a phenol compound, said esters having formulae (IB) or (IIB):
- ##STR39## wherein R.sub.1, R.sub.2, R.sub.11, and R.sub.12 are each independently selected from the group consisting of hydrogen, OD, halogen, lower alkyl group having 1 to 4 carbon atoms, lower alkyl ether groups having 1 to 4 carbon atoms and lower alkyl thioether groups having 1 to 4 carbon atoms;
- wherein R.sub.3, R.sub.4, R.sub.5, R.sub.6, R.sub.7, R.sub.8, R.sub.9, R.sub.10, R.sub.13, and R.sub.14 are each independently selected from the group consisting of hydrogen, halogen, lower alkyl groups having 1 to 4 carbon atoms, lower alkyl ether groups having 1 to 4 carbon atoms;
- and lower alkyl thioether groups having 1 to 4 carbon groups;
- wherein x and y are each independently selected from an integer from the group 0, 1, 2, 3, and 4;
- wherein Ra, Rb, Rc, and Rd are each independently selected from hydrogen and a lower alkyl group having 1 to 4 carbon atoms;
- wherein v and w are each independently selected from an integer from the group 0 and 1 and each sum of v and w on a fused ring is 1 or 2;
- and
- wherein A and B are each independently selected from the group consisting of oxygen, sulfur, and a methylene radical;
- wherein each --OD group is a hydroxyl or an o-quinonediazide sulfonic acid ester group wherein each D is selected from the group consisting of napthoquinonediazide sulfonyl group or benzoquinonediazide sulfonyl group provided that at least one --OD group is an o-quinonediazide sulfonic acid ester group;
- and
- wherein the amount of photosensitive compound is from about 5% to about 40% by weight, based on the total solid content of said radiation sensitive mixture.
A positive photoresist composition comprising an admixture of an alkali soluble resin and a photoactive compound comprising quinonediazide sulfonic acid ester of a phenol compound;
- wherein:
- (a) said phenol compound has no less than four phenolic hydroxyl groups, and (b) wherein a HPLC peak area corresponding to the quinonediazide sulfonic acid triesters is greater than or equal to 50% of all HPLC peak areas corresponding to the photoactive compounds in said HPLC spectrum;
- said HPLC spectrum measured with a primary detector using UV light having the wavelength of 254 nm.
A positive photoresist composition comprising an admixture of an alkali soluble resin and a photoactive compound comprising quinonediazide sulfonic acid esters of two or more phenolic compounds, wherein:
- (a) at least one of said phenolic compounds has three phenolic hydroxyl groups and at least one of said phenolic compounds has four phenolic hydroxyl groups;
- (b) the HPLC peak area corresponding to quinonediazide sulfonic acid triesters of the phenolic compounds is greater than or equal to 45% of the total HPLC peak area of all quinonediazide sulfonic acid esters;
- (c) the HPLC peak area corresponding to quinonediazide sulfonic acid diesters is less than or equal to 40% of the total HPLC peak area of all quinonediazide sulfonic acid esters;
- and
- (d) the HPLC peak area corresponding to the quinonediazide sulfonic acid triester of the phenolic compounds having 3 hydroxyl groups is less than or equal to 20% of the total HPLC peak area of all quinonediazide sulfonic acid esters;
- said HPLC spectrum measured with a primary detector using UV light having the wavelength of 254 nm.
Dependencies are inferred from the claim text.